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Org Lett. 2013 Feb 1;15(3):524-7. doi: 10.1021/ol3033412. Epub 2013 Jan 17.

A bifunctional Lewis acid induced cascade cyclization to the tricyclic core of ent-kaurenoids and its application to the formal synthesis of (±)-platensimycin.

Author information

1
Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen University Town, Xili, Shenzhen 518055, China.

Abstract

A mild and efficient bifunctional Lewis acid induced cascade cyclization reaction has been developed for construction of the tricyclic core of ent-kaurenoids. With ZnBr(2) as the bifunctional Lewis acid, a series of substituted enones and dienes underwent cascade cyclization smoothly at room temperature and provided the tricyclic products in one pot with good yields (75-91%) and high diastereoselectivity. The cyclized product has been successfully employed for the formal synthesis of (±)-platensimycin.

PMID:
23327558
DOI:
10.1021/ol3033412
[Indexed for MEDLINE]

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