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. 2010 Mar 8;49(11):2000-3.
doi: 10.1002/anie.200906818.

Total synthesis of the polycyclic fungal metabolite (+/-)-communesin F

Peng Liu  1 , Jae Hong Seo, Steven M Weinreb
Affiliations

Total synthesis of the polycyclic fungal metabolite (+/-)-communesin F

Peng Liu et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Figure 1
Figure 1
The communesin family of natural products.
Scheme 1
Scheme 1
a) Pd(PPh3)4, DME, H2O, Na2CO3, 80°C, 10, 98%; b) LiOH, H2O, MeOH, 50°C, 86%; c) SOCl2, reflux; i-Pr2NEt, CH2Cl2, rt, 12, 87%; d) ClCOOEt, CH2Cl2, 0°C-rt, 96%; e) NaH, THF, MeI, 0°C-rt, 92%; f) Pd(OAc)2, PPh3, DMA, K2CO3, n-Bu4NBr, 150°C, 90%. DME = 1,2-dimethoxyethane; DMA = N,N-dimethylacetamide
Scheme 2
Scheme 2
a) 5% Pt/C, H2 (40 atm) PhMe, rt; b) Boc2O, K2CO3, THF, H2O, 60°C, 87% (2 steps); c) AlH3·Me2NEt, THF, 0°C-rt, 74%; d) 1 N KOH, EtOH, 94°C; e)NCN3, MeCN, rt, 93% (2 steps); f) 1 N KOH, EtOH, 94°C, 60%; g) Boc2O, LiHMDS, THF, rt, 95%; h) KOt-Bu, THF, allyl iodide, -78°C-rt, 87%; i) 1 N KOH, EtOH, 80°C, 94%; j) OsO4, NMO, THF, H2O; NaIO4, rt; k) NaBH4, EtOH, 0°C; l) MsCl, NEt3, CH2Cl2, 0°C, 83% (3 steps). Boc = tert-butoxycarbonyl; LiHMDS = lithium hexamethyldisilazide; NMO = N-methylmorpholine N-oxide; MsCl = methanesulfonyl chloride.
Scheme 3
Scheme 3
a) Pearlman’s catalyst, H2, THF, rt; b) Dess-Martin reagent, CH2Cl2, rt, 75% (2 steps); c) NaN3, DMF, 90°C, 61%; d) Me2CO, 10% NaOH/H2 O, 60°C, 93%; e) Boc2O, LiHMDS, THF, rt, 81%; f) PMe3, THF, H2O, 70°C, 88%. Dess-Martin reagent = 1,1,1-triacetoxy-1,1-dihydro-1,2-benzodioxol-3(1H)-one.
Scheme 4
Scheme 4
a) MeLi, THF, −78°C, 73%; b) PPTS, CHCl3, rt, 62%; c) Me3OBF4, i-Pr2NEt, CH2Cl2, rt, 86%; d) 5% TFA/CH2Cl2, rt, 88%; e) NaBH4, Ac2O, HOAc; f) 40% TFA/CH2Cl2, rt, 66% (2 steps). PPTS = pyridinium p-toluenesulfonate; TFA = trifluoroacetic acid.
See this image and copyright information in PMC

References

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    1. For studies on the biosynthesis of the communesins see: Wigley LJ, Mantle PG, Perry DA. Phytochemistry. 2006;67:561.See also ref. .

    1. For synthetic studies on the communesins and/or the related metabolite perophoramidine see: May JA, Zeidan RK, Stoltz BM. Tetrahedron Lett. 2003;44:1203.May JA, Stoltz BM. Tetrahedron. 2006;62:5262.Yang J, Song H, Xiao X, Wang J, Qin Y. Org Lett. 2006;8:2187.Crawley SL, Funk RL. Org Lett. 2003;5:3169.Fuchs JR, Funk RL. J Am Chem Soc. 2004;126:5068.Sabhi A, Novikov A, Rainier JD. Angew Chem Int Ed. 2006;45:4317.Artman GD, III, Weinreb SM. Org Lett. 2003;5:1523.Seo JH, Artman GD, III, Weinreb SM. J Org Chem. 2006;71:8891.Evans MA, Sacher JR, Weinreb SM. Tetrahedron. 2009;65:6712.George JH, Adlington RM. Synlett. 2008:2093.

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