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. 2018 Jul 11;24(39):9773-9777.
doi: 10.1002/chem.201802083. Epub 2018 Jun 8.

Total Syntheses of Trichorabdal A and Maoecrystal Z

Affiliations

Total Syntheses of Trichorabdal A and Maoecrystal Z

Zhe Lv et al. Chemistry. .

Abstract

This work reports the total syntheses of Isodon diterpenes trichorabdal A and maoecrystal Z via a common bicyclo[3.2.1]octane intermediate, which chemically bridges the two distinct structures through a retro-aldol/aldol reaction cascade. Other synthetic features include an efficient cross-ring radical cyclization for rapid construction of an all carbon quaternary center commonly seen in Isodon diterpenoids, a challenging Ueno-Stork cyclization on to a sensitive 1,6-enone system, as well as a serial of chemoselective functional group manipulations in complex chemical environments.

Keywords: aldol reaction; chemoselectivity; cyclization; radicals; retroreactions; total synthesis.

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