Vijay P. Chavan

A chiron approach to the total synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin.

A general, efficient, and common strategy for the synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin is reported here. The strategy involves the synthesis of a key building block alkyne from a cheap chiral pool material, D-glucono-δ-lactone, Dötz benzannulation, oxa-Pictet-Spengler reaction, and H(2)SO(4)-mediated epimerization.

Stereoselective synthesis of (−)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3

A stereoselective synthesis of (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L, the monomeric unit of cardinalin 3 has been described. The synthesis is completed in 7 steps with 10.5% and 13% overall yields for (-)-1-epi-ventiloquinone L and (+)-ventiloquinone L respectively. The key steps involve Dötz benzannulation of carbene 5 with alkyne 6 to give a substituted naphthalene moiety and oxa-Pictet-Spengler reaction to install the 1,3-dimethylpyran moiety.

Short eight-steps total synthesis of racemic asteriscunolide C

ABSTRACT A concise total synthesis of racemic asteriscunolide C in eight steps has been described starting from neopentane diol involving an efficient Yamaguchi esterification using an aldehyde-acid, intramolecular Horner–Wittig–Emmons olefination, and a late stage ring-closing metathesis to construct the strained 11-membered ring with one Z- and two E-double bonds. GRAPHICAL ABSTRACT