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Chem Asian J. 2012 Oct;7(10):2334-40. doi: 10.1002/asia.201200364. Epub 2012 Jul 3.

Diastereoselective total synthesis of (±)-schindilactone A, Part 2: Construction of the fully functionalized CDEFGH ring system.

Author information

1
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science and Peking-Tsinghua Center for Life Sciences at College of Chemistry of Peking University, Chengfu Road, 202, Beijing, 100871, China.

Abstract

The successful synthesis of the highly complex model compound (2) of the CEFGH ring system of schindilactone A (1) is described. Several synthetic methodologies were developed and applied to achieve this goal, including ring-closing metathesis (RCM) and Co-thiourea-catalyzed Pauson-Khand reactions. Furthermore, two independent approaches were developed for the construction of the GH ring of model compound 2, the key steps of which included Pd-thiourea-catalyzed carbonylative annulation, methylation, and sequential RCM/oxa-Michael-addition reactions. The chemistry developed herein has provided a greater understanding of the synthesis of schindilactone A (1) and its analogous compounds of the same family.

PMID:
22761018
DOI:
10.1002/asia.201200364
[Indexed for MEDLINE]

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