Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition

doi:10.1016/j.tet.2010.04.131

. 2010 Aug 14;66(33):6647-6655.

doi: 10.1016/j.tet.2010.04.131.

Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition

David B Freeman¹, Alexandra A Holubec, Matthew W Weiss, Julie A Dixon, Akio Kakefuda, Masami Ohtsuka, Munenori Inoue, Rishi G Vaswani, Hidenori Ohki, Brian D Doan, Sarah E Reisman, Brian M Stoltz, Joshua J Day, Ran N Tao, Noah A Dieterich, John L Wood

Affiliations

PMID: 20733933
PMCID: PMC2924776
DOI: 10.1016/j.tet.2010.04.131

Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition

David B Freeman et al. Tetrahedron. 2010.

. 2010 Aug 14;66(33):6647-6655.

doi: 10.1016/j.tet.2010.04.131.

Authors

Affiliation

¹ Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.

PMID: 20733933
PMCID: PMC2924776
DOI: 10.1016/j.tet.2010.04.131

Abstract

Described is the construction of the N-methylwelwitindolinone C core via an efficient strategy that employs a sequential rhodium carbenoid-mediated O-H insertion, Claisen rearrangement and transannular [3+2] nitrone cycloaddition.

PubMed Disclaimer

Figures

See this image and copyright information in PMC

Cited by

Isatin derivatives in reactions with phosphorus(III-V) compounds.
Musin LI, Bogdanov AV, Mironov VF. Musin LI, et al. Chem Heterocycl Compd (N Y). 2015;51(5):421-439. doi: 10.1007/s10593-015-1717-2. Epub 2015 Jun 19. Chem Heterocycl Compd (N Y). 2015. PMID: 32214418 Free PMC article.
A unified route to the welwitindolinone alkaloids: total syntheses of (-)-N-methylwelwitindolinone C isothiocyanate, (-)-N-methylwelwitindolinone C isonitrile, and (-)-3-hydroxy-N-methylwelwitindolinone C isothiocyanate.
Allan KM, Kobayashi K, Rawal VH. Allan KM, et al. J Am Chem Soc. 2012 Jan 25;134(3):1392-5. doi: 10.1021/ja210793x. Epub 2012 Jan 11. J Am Chem Soc. 2012. PMID: 22235963 Free PMC article.
Lessons Learned while Traversing the Welwitindolinone Alkaloids Obstacle Course.
Bhat V, Mackay JA, Rawal VH. Bhat V, et al. Tetrahedron. 2011 Dec 30;67(52):100997-10104. doi: 10.1016/j.tet.2011.09.088. Epub 2011 Sep 24. Tetrahedron. 2011. PMID: 22962500 Free PMC article.
Directed oxidative cyclizations to C2- or C4-positions of indole: efficient construction of the bicyclo[4.3.1]decane core of welwitindolinones.
Bhat V, Mackay JA, Rawal VH. Bhat V, et al. Org Lett. 2011 Jun 17;13(12):3214-7. doi: 10.1021/ol201122f. Epub 2011 May 26. Org Lett. 2011. PMID: 21615098 Free PMC article.
Total synthesis of oxidized welwitindolinones and (-)-N-methylwelwitindolinone C isonitrile.
Quasdorf KW, Huters AD, Lodewyk MW, Tantillo DJ, Garg NK. Quasdorf KW, et al. J Am Chem Soc. 2012 Jan 25;134(3):1396-9. doi: 10.1021/ja210837b. Epub 2012 Jan 11. J Am Chem Soc. 2012. PMID: 22235964 Free PMC article.

See all "Cited by" articles

References

1. Stratmann K, Moore RE, Bonjouklian R, Deeter JB, Patterson GML, Shaffer S, Smith CD, Smitka TA. J Am Chem Soc. 1994;116:9935–9942.
1. Jimenez JI, Huber U, Moore RE, Patterson GML. J Nat Prod. 1999;62:569–572. - PubMed
1. Jimenez JL, Huber U, Moore RE, Patterson GML. J Nat Prod. 1999;62:940–940. - PubMed
1. Wood JL, Holubec AA, Stoltz BM, Weiss MM, Dixon JA, Doan BD, Shamji MF, Chen JM, Heffron TP. J Am Chem Soc. 1999;121:6326–6327.
1. Ready JM, Reisman SE, Hirata M, Weiss MM, Tamaki K, Ovaska TV, Wood JL. Angew Chem, Int Ed. 2004;43:1270–1272. - PubMed

Grants and funding

R01 CA093591/CA/NCI NIH HHS/United States

LinkOut - more resources

Full Text Sources
- Europe PubMed Central
- PubMed Central

[1] Stratmann K, Moore RE, Bonjouklian R, Deeter JB, Patterson GML, Shaffer S, Smith CD, Smitka TA. J Am Chem Soc. 1994;116:9935–9942.

[2] Stratmann K, Moore RE, Bonjouklian R, Deeter JB, Patterson GML, Shaffer S, Smith CD, Smitka TA. J Am Chem Soc. 1994;116:9935–9942.

[3] Jimenez JI, Huber U, Moore RE, Patterson GML. J Nat Prod. 1999;62:569–572. - PubMed

[4] Jimenez JI, Huber U, Moore RE, Patterson GML. J Nat Prod. 1999;62:569–572. - PubMed

[5] Jimenez JL, Huber U, Moore RE, Patterson GML. J Nat Prod. 1999;62:940–940. - PubMed

[6] Jimenez JL, Huber U, Moore RE, Patterson GML. J Nat Prod. 1999;62:940–940. - PubMed

[7] Wood JL, Holubec AA, Stoltz BM, Weiss MM, Dixon JA, Doan BD, Shamji MF, Chen JM, Heffron TP. J Am Chem Soc. 1999;121:6326–6327.

[8] Wood JL, Holubec AA, Stoltz BM, Weiss MM, Dixon JA, Doan BD, Shamji MF, Chen JM, Heffron TP. J Am Chem Soc. 1999;121:6326–6327.

[9] Ready JM, Reisman SE, Hirata M, Weiss MM, Tamaki K, Ovaska TV, Wood JL. Angew Chem, Int Ed. 2004;43:1270–1272. - PubMed

[10] Ready JM, Reisman SE, Hirata M, Weiss MM, Tamaki K, Ovaska TV, Wood JL. Angew Chem, Int Ed. 2004;43:1270–1272. - PubMed

Save citation to file

Email citation

Add to Collections

Add to My Bibliography

Your saved search

Create a file for external citation management software

Your RSS Feed

Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition

Affiliation

Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition

Authors

Affiliation

Abstract

Figures

Similar articles

Cited by

References

Grants and funding

LinkOut - more resources

Full Text Sources