Total synthesis of dipiperamide A and revision of stereochemical assignment

[Display omitted] The first total synthesis of dipiperamide A has been achieved by employing a solid-state photodimerization of an ( E)-cinnamic acid derivative. This critical step results in the cyclobutane ring, which exists in the natural product, with full control of the regio- and stereochemist...

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Bibliographic Details
Published inTetrahedron letters Vol. 46; no. 1; pp. 57 - 59
Main Authors Takahashi, Masaki, Ichikawa, Masaya, Aoyagi, Sakae, Kibayashi, Chihiro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.01.2005
Elsevier
Subjects
Chemistry
Chemistry, Organic
Cyclobutane ring
CYP inhibitor
Dipiperamide A
Physical Sciences
Science & Technology
Solid-state photodimerization
Solid-state photodimerization
Cyclobutane ring
CYP inhibitor
Dipiperamide A
dipiperamide A
solidstate photodimerization
TOPOCHEMISTRY
BISALKALOIDS
cyclobutane ring
TRANS-CINNAMIC ACIDS
WHITE PEPPER
PIPER-NIGRUM
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Summary:[Display omitted] The first total synthesis of dipiperamide A has been achieved by employing a solid-state photodimerization of an ( E)-cinnamic acid derivative. This critical step results in the cyclobutane ring, which exists in the natural product, with full control of the regio- and stereochemistry at the four stereogenic centers. Results from these studies indicate that the proposed stereostructure of natural dipiperamide A should be revised to the structure originally assigned to dipiperamide B.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.11.042