Total synthesis of himandravine.

Journal Article (Journal Article)

[reaction: see text] The first total synthesis of (+)-himandravine (1) is described, starting from (2S,6S)-cis-2-formyl-6-methyl-N-Boc-piperidine (8) in 11 linear steps and 17% overall yield. The key step involves a highly diastereoselective intramolecular Diels-Alder reaction of the key intermediate 5 that contains the entire latent carbon framework and functional group substitution of himandravine.

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Duke Authors

McPhail, Andrew T.

Cited Authors

Chackalamannil, S; Davies, R; McPhail, AT

Published Date

May 2001

Published In

Organic Letters

Volume / Issue

3 / 10

Start / End Page

1427 - 1429

PubMed ID

11388833

Electronic International Standard Serial Number (EISSN)

1523-7052

International Standard Serial Number (ISSN)

1523-7060

Digital Object Identifier (DOI)

10.1021/ol010038w

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