Total Synthesis of Staurosporine

Abstracted with permission from J. Am. Chan. Soc., 199S, 117, 552 1995 American Chemical Society 

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The first total synthesis of staurosporine and of e/it-staurosporine has been reported in full (see Vol. 29, p. 378). The glycal-derived epoxide 191 (from dimethyldioxirane epoxidation of the precursor glycal) was treated with the sodium salt of 190 and the product, 192, was then elaborated using iodoamina-tion as the the key cyclization step, radical deiodination then affording 193, an intermediate for synthesis of e r-staurosporine. ... 

First total synthesis of staurosporine and ent-staurosporine (Danishefsky et al., 1995)... 

Rajeshwaran GG, Mohanakrishnan AK. S3mthetic studies on indolocarbazoles Total synthesis of staurosporine aglycon. Qrg. Lett. 2011 13 (6) 1418-1421. 

The total synthesis of litseaverticillols D, F and G (172 and 173), which are natural products with anti-HIV activity, was achieved recently via a singlet oxygen initiated cascade proposed to be biomimetic (Scheme 64). Finally, allylic alcohols 174a and 174b (Scheme 64) were isolated in a 4/1 ratio via a stereoselective singlet oxygen ene reaction. Stereoisomer 174a is an intermediate in the synthetic route of staurosporine, which is a bioactive alkaloid with hypotensive, antimicrobial and cell cytotoxic properties. 

Wood JL, Stolz BM, Goodman SN, Qnwuene K. Design and implementation of an effective synthetic approach to pyranosylated indolocarbazoles Total synthesis of (-1-)-RK286c, (-i-)-MLR-52, (-i-)-Staurosporine, and (-)-TAN-1030a. J. /Vm. Chem. Soc. 1997 119 9652-9661. 

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