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J Org Chem. 2013 Jun 7;78(11):5492-504. doi: 10.1021/jo4006156. Epub 2013 May 23.

Asymmetric total synthesis of caribenol A via an intramolecular Diels-Alder reaction.

Author information

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

Abstract

A total synthesis of the caribenol A (1), a novel natural product with an intriguing tetracyclic framework, has been achieved. The synthesis features an intramolecular Diels-Alder (IMDA) reaction for the facile construction of the tricyclic [5-7-6] skeleton of caribenol A (1) and a biomimetic oxidation reaction for the formation of the 2-hydroxyfuran-2(5H)-one motif of caribenol A (1) as key steps. This synthetic approach also reveals that the sp(2) carbon at C(2) in substrate 8 is a critical factor for the formation of the tricyclic [5-7-6] skeleton in 7.

PMID:
23672454
DOI:
10.1021/jo4006156
[Indexed for MEDLINE]

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