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Chem Asian J. 2013 Sep;8(9):1972-5. doi: 10.1002/asia.201300441. Epub 2013 Jun 11.

Asymmetric, protecting-group-free total synthesis of (+)-caribenol A.

Author information

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

Abstract

Caribenol Queen: A new asymmetric, protecting-group-free synthesis of the marine tetracyclic diterpenoid (+)-caribenol A (1) has been achieved. The enantioselective synthesis employed (S)-methyl 1-methyl-2-oxocyclopent-3-enecarboxylate as a chiral scaffold, and an intramolecular Diels-Alder (IMDA) reaction of substrate 3 afforded the [5.7.6] tricyclic core in compound 2.

KEYWORDS:

Diels-Alder reaction; asymmetric synthesis; intramolecular; synthetic methods; total synthesis

PMID:
23761011
DOI:
10.1002/asia.201300441
[Indexed for MEDLINE]

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