Total synthesis of the tetracyclic sesquiterpene (±)-punctaporonin C

Martin Fleck; Thorsten Bach

doi:10.1002/anie.200801534

Total synthesis of the tetracyclic sesquiterpene (±)-punctaporonin C

Martin Fleck, Thorsten Bach

Chair of Organic Chemistry 1

Technical University of Munich

Research output: Contribution to journal › Article › peer-review

43 Scopus citations

Abstract

Tailor made for the target molecule 2, the carbon skeleton of the epoxide 1 was integrated entirely into the natural product. A regioselective intramolecular [2+2] photocycloaddition and subsequent Wacker oxidation enabled the specific and successive incorporation of the two terminal double bonds of 1 into the unusual oxatetracyclo [6.3.2.0^1,4.0^5,13] tridecane skeleton of 2, which was synthesized in 24 steps and 2.0% overall yield. TBDMS = tert-butyldimethylsilyl. (Chemical Equation Presented)

Original language	English
Pages (from-to)	6189-6191
Number of pages	3
Journal	Angewandte Chemie International Edition in English
Volume	47
Issue number	33
DOIs	https://doi.org/10.1002/anie.200801534
State	Published - 4 Aug 2008

Keywords

Naturalproducts
Photochemistry
Regioselectivity
Terpenoids
Total synthesis

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10.1002/anie.200801534

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KW - Naturalproducts

KW - Photochemistry

KW - Regioselectivity

KW - Terpenoids

KW - Total synthesis

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Total synthesis of the tetracyclic sesquiterpene (±)-punctaporonin C

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Keywords

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