Synthesis of functionalized cyclohexenone core of welwitindolinones via rhodium-catalyzed [5 + 1] cycloaddition

doi:10.1021/ol301614v

. 2012 Jul 20;14(14):3756-9.

doi: 10.1021/ol301614v. Epub 2012 Jul 11.

Synthesis of functionalized cyclohexenone core of welwitindolinones via rhodium-catalyzed [5 + 1] cycloaddition

Min Zhang¹, Weiping Tang

Affiliations

PMID: 22783971
PMCID: PMC3480994
DOI: 10.1021/ol301614v

Synthesis of functionalized cyclohexenone core of welwitindolinones via rhodium-catalyzed [5 + 1] cycloaddition

Min Zhang et al. Org Lett. 2012.

. 2012 Jul 20;14(14):3756-9.

doi: 10.1021/ol301614v. Epub 2012 Jul 11.

Authors

Min Zhang¹, Weiping Tang

Affiliation

¹ School of Pharmacy, University of Wisconsin , Madison, Wisconsin 53705, United States.

PMID: 22783971
PMCID: PMC3480994
DOI: 10.1021/ol301614v

Abstract

The cyclohexenone core of welwitindolinones was synthesized by a Rh(I)-catalyzed [5 + 1]-cycloaddition of an allenylcyclopropane with CO. A pentasubstituted cyclopropane was prepared successfully by a Rh(II)-catalyzed intramolecular cyclopropanation of alkenes with chlorodiazoacetates.

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Figures

**Scheme 1**
Proposed Strategies for Welwitindolinones

**Scheme 2**
Intramolecular Cyclopropanation of an Alkene Substituted with a N-Methyl Indole

**Scheme 3**
Intramolecular Cyclopropanation of an Alkene Substituted with a N-Boc protected Indole

**Scheme 4**
Preparation of Penta-substituted Allenylcyclopropane

**Scheme 5**
Rh-catalyzed [5+1] cycloaddition of Allenylcyclopropane and CO

See this image and copyright information in PMC

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References

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1. For efforts towards the synthesis of welwitindolinones, see: Konopelski JP, Deng HB, Schiemann K, Keane JM, Olmstead MM. Synlett. 1998:1105.Wood JL, Holubec AA, Stoltz BM, Weiss MM, Dixon JA, Doan BD, Shamji MF, Chen JM, Heffron TP. J Am Chem Soc. 1999;121:6326.Kaoudi T, Quiclet-Sire B, Seguin S, Zard SZ. Angew Chem Int Ed. 2000;39:731.Jung ME, Slowinski F. Tetrahedron Lett. 2001;42:6835.Deng HB, Konopelski JP. Org Lett. 2001;3:3001.Lopez-Alvarado P, Garcia-Granda S, Alvarez-Rua C, Avendano C. Eur J Org Chem. 2002:1702.Ready JM, Reisman SE, Hirata M, Weiss MM, Tamaki K, Ovaska TV, Wood JL. Angew Chem Int Ed. 2004;43:1270.Mackay JA, Bishop RL, Rawal VH. Org Lett. 2005;7:3421.Baudoux J, Blake AJ, Simpkins NS. Org Lett. 2005;7:4087.Greshock TJ, Funk RL. Org Lett. 2006;8:2643.Lauchli R, Shea KJ. Org Lett. 2006;8:5287.Xia J, Brown LE, Konopelski JP. J Org Chem. 2007;72:6885.Richter JM, Ishihara Y, Masuda T, Whitefield BW, Llamas T, Pohjakallio A, Baran PS. J Am Chem Soc. 2008;130:17938.Boissel V, Simpkins NS, Bhalay G, Blake AJ, Lewis W. Chem Commun. 2009:1398.Boissel V, Simpkins NS, Bhalay G. Tetrahedron Lett. 2009;50:3283.Tian X, Huters AD, Douglas CJ, Garg NK. Org Lett. 2009;11:2349.Trost BM, Mcdougall PJ. Org Lett. 2009;11:3782.Brailsford JA, Lauchli R, Shea KJ. Org Lett. 2009;11:5330.Freeman DB, Holubec AA, Weiss MW, Dixon JA, Kakefuda A, Ohtsuka M, Inoue M, Vaswani RG, Ohki H, Doan BD, Reisman SE, Stoltz BM, Day JJ, Tao RN, Dieterich NA, Wood JL. Tetrahedron. 2010;66:6647.Heidebrecht RW, Gulledge B, Martin SF. Org Lett. 2010;12:2492.Ruiz M, Lopez-Alvarado P, Menendez JC. Org Biomol Chem. 2010;8:4521.
1. Baran PS, Richter JM. J Am Chem Soc. 2005;127:15394. - PubMed
2. Reisman SE, Ready JM, Hasuoka A, Smith CJ, Wood JL. J Am Chem Soc. 2006;128:1448. - PubMed
3. Baran PS, Maimone TJ, Richter JM. Nature. 2007;446:404. - PubMed
4. Reisman SE, Ready JM, Weiss MM, Hasuoka A, Hirata M, Tamaki K, Ovaska TV, Smith CJ, Wood JL. J Am Chem Soc. 2008;130:2087. - PubMed
1. Bhat V, Allan KM, Rawal VH. J Am Chem Soc. 2011;133:5798. - PMC - PubMed
2. Bhat V, Mackay JA, Rawal VH. Org Lett. 2011;13:3214. - PMC - PubMed
3. Bhat V, Rawal VH. Chem Commun. 2011;47:9705. - PubMed
4. Bhat V, Mackay JA, Rawal VH. Tetrahedron. 2011;67:10097. - PMC - PubMed
5. Allan KM, Kobayashi K, Rawal VH. J Am Chem Soc. 2012;134:1392. - PMC - PubMed

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[1] Stratmann K, Moore RE, Bonjouklian R, Deeter JB, Patterson GML, Shaffer S, Smith CD, Smitka TA. J Am Chem Soc. 1994;116:9935.

Jimenez JI, Huber U, Moore RE, Patterson GML. J Nat Prod. 1999;62:569. - PubMed

[2] Stratmann K, Moore RE, Bonjouklian R, Deeter JB, Patterson GML, Shaffer S, Smith CD, Smitka TA. J Am Chem Soc. 1994;116:9935.

[3] Jimenez JI, Huber U, Moore RE, Patterson GML. J Nat Prod. 1999;62:569. - PubMed

[4] Smith CD, Zilfou JT, Stratmann K, Patterson GML, Moore RE. Mol Pharmacol. 1995;47:241. - PubMed

Zhang XQ, Smith CD. Mol Pharmacol. 1996;49:288. - PubMed

[5] Smith CD, Zilfou JT, Stratmann K, Patterson GML, Moore RE. Mol Pharmacol. 1995;47:241. - PubMed

[6] Zhang XQ, Smith CD. Mol Pharmacol. 1996;49:288. - PubMed

[7] For efforts towards the synthesis of welwitindolinones, see: Konopelski JP, Deng HB, Schiemann K, Keane JM, Olmstead MM. Synlett. 1998:1105.Wood JL, Holubec AA, Stoltz BM, Weiss MM, Dixon JA, Doan BD, Shamji MF, Chen JM, Heffron TP. J Am Chem Soc. 1999;121:6326.Kaoudi T, Quiclet-Sire B, Seguin S, Zard SZ. Angew Chem Int Ed. 2000;39:731.Jung ME, Slowinski F. Tetrahedron Lett. 2001;42:6835.Deng HB, Konopelski JP. Org Lett. 2001;3:3001.Lopez-Alvarado P, Garcia-Granda S, Alvarez-Rua C, Avendano C. Eur J Org Chem. 2002:1702.Ready JM, Reisman SE, Hirata M, Weiss MM, Tamaki K, Ovaska TV, Wood JL. Angew Chem Int Ed. 2004;43:1270.Mackay JA, Bishop RL, Rawal VH. Org Lett. 2005;7:3421.Baudoux J, Blake AJ, Simpkins NS. Org Lett. 2005;7:4087.Greshock TJ, Funk RL. Org Lett. 2006;8:2643.Lauchli R, Shea KJ. Org Lett. 2006;8:5287.Xia J, Brown LE, Konopelski JP. J Org Chem. 2007;72:6885.Richter JM, Ishihara Y, Masuda T, Whitefield BW, Llamas T, Pohjakallio A, Baran PS. J Am Chem Soc. 2008;130:17938.Boissel V, Simpkins NS, Bhalay G, Blake AJ, Lewis W. Chem Commun. 2009:1398.Boissel V, Simpkins NS, Bhalay G. Tetrahedron Lett. 2009;50:3283.Tian X, Huters AD, Douglas CJ, Garg NK. Org Lett. 2009;11:2349.Trost BM, Mcdougall PJ. Org Lett. 2009;11:3782.Brailsford JA, Lauchli R, Shea KJ. Org Lett. 2009;11:5330.Freeman DB, Holubec AA, Weiss MW, Dixon JA, Kakefuda A, Ohtsuka M, Inoue M, Vaswani RG, Ohki H, Doan BD, Reisman SE, Stoltz BM, Day JJ, Tao RN, Dieterich NA, Wood JL. Tetrahedron. 2010;66:6647.Heidebrecht RW, Gulledge B, Martin SF. Org Lett. 2010;12:2492.Ruiz M, Lopez-Alvarado P, Menendez JC. Org Biomol Chem. 2010;8:4521.

[8] For efforts towards the synthesis of welwitindolinones, see: Konopelski JP, Deng HB, Schiemann K, Keane JM, Olmstead MM. Synlett. 1998:1105.Wood JL, Holubec AA, Stoltz BM, Weiss MM, Dixon JA, Doan BD, Shamji MF, Chen JM, Heffron TP. J Am Chem Soc. 1999;121:6326.Kaoudi T, Quiclet-Sire B, Seguin S, Zard SZ. Angew Chem Int Ed. 2000;39:731.Jung ME, Slowinski F. Tetrahedron Lett. 2001;42:6835.Deng HB, Konopelski JP. Org Lett. 2001;3:3001.Lopez-Alvarado P, Garcia-Granda S, Alvarez-Rua C, Avendano C. Eur J Org Chem. 2002:1702.Ready JM, Reisman SE, Hirata M, Weiss MM, Tamaki K, Ovaska TV, Wood JL. Angew Chem Int Ed. 2004;43:1270.Mackay JA, Bishop RL, Rawal VH. Org Lett. 2005;7:3421.Baudoux J, Blake AJ, Simpkins NS. Org Lett. 2005;7:4087.Greshock TJ, Funk RL. Org Lett. 2006;8:2643.Lauchli R, Shea KJ. Org Lett. 2006;8:5287.Xia J, Brown LE, Konopelski JP. J Org Chem. 2007;72:6885.Richter JM, Ishihara Y, Masuda T, Whitefield BW, Llamas T, Pohjakallio A, Baran PS. J Am Chem Soc. 2008;130:17938.Boissel V, Simpkins NS, Bhalay G, Blake AJ, Lewis W. Chem Commun. 2009:1398.Boissel V, Simpkins NS, Bhalay G. Tetrahedron Lett. 2009;50:3283.Tian X, Huters AD, Douglas CJ, Garg NK. Org Lett. 2009;11:2349.Trost BM, Mcdougall PJ. Org Lett. 2009;11:3782.Brailsford JA, Lauchli R, Shea KJ. Org Lett. 2009;11:5330.Freeman DB, Holubec AA, Weiss MW, Dixon JA, Kakefuda A, Ohtsuka M, Inoue M, Vaswani RG, Ohki H, Doan BD, Reisman SE, Stoltz BM, Day JJ, Tao RN, Dieterich NA, Wood JL. Tetrahedron. 2010;66:6647.Heidebrecht RW, Gulledge B, Martin SF. Org Lett. 2010;12:2492.Ruiz M, Lopez-Alvarado P, Menendez JC. Org Biomol Chem. 2010;8:4521.

[9] Baran PS, Richter JM. J Am Chem Soc. 2005;127:15394. - PubMed

Reisman SE, Ready JM, Hasuoka A, Smith CJ, Wood JL. J Am Chem Soc. 2006;128:1448. - PubMed

Baran PS, Maimone TJ, Richter JM. Nature. 2007;446:404. - PubMed

Reisman SE, Ready JM, Weiss MM, Hasuoka A, Hirata M, Tamaki K, Ovaska TV, Smith CJ, Wood JL. J Am Chem Soc. 2008;130:2087. - PubMed

[10] Baran PS, Richter JM. J Am Chem Soc. 2005;127:15394. - PubMed

[11] Reisman SE, Ready JM, Hasuoka A, Smith CJ, Wood JL. J Am Chem Soc. 2006;128:1448. - PubMed

[12] Baran PS, Maimone TJ, Richter JM. Nature. 2007;446:404. - PubMed

[13] Reisman SE, Ready JM, Weiss MM, Hasuoka A, Hirata M, Tamaki K, Ovaska TV, Smith CJ, Wood JL. J Am Chem Soc. 2008;130:2087. - PubMed

[14] Bhat V, Allan KM, Rawal VH. J Am Chem Soc. 2011;133:5798. - PMC - PubMed

Bhat V, Mackay JA, Rawal VH. Org Lett. 2011;13:3214. - PMC - PubMed

Bhat V, Rawal VH. Chem Commun. 2011;47:9705. - PubMed

Bhat V, Mackay JA, Rawal VH. Tetrahedron. 2011;67:10097. - PMC - PubMed

Allan KM, Kobayashi K, Rawal VH. J Am Chem Soc. 2012;134:1392. - PMC - PubMed

[15] Bhat V, Allan KM, Rawal VH. J Am Chem Soc. 2011;133:5798. - PMC - PubMed

[16] Bhat V, Mackay JA, Rawal VH. Org Lett. 2011;13:3214. - PMC - PubMed

[17] Bhat V, Rawal VH. Chem Commun. 2011;47:9705. - PubMed

[18] Bhat V, Mackay JA, Rawal VH. Tetrahedron. 2011;67:10097. - PMC - PubMed

[19] Allan KM, Kobayashi K, Rawal VH. J Am Chem Soc. 2012;134:1392. - PMC - PubMed

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Synthesis of functionalized cyclohexenone core of welwitindolinones via rhodium-catalyzed [5 + 1] cycloaddition

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Synthesis of functionalized cyclohexenone core of welwitindolinones via rhodium-catalyzed [5 + 1] cycloaddition

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Abstract

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References

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