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Application of the taraxerane-oleanane rearrangement to the synthesis of seco-oleanane triterpenoids from taraxerone

http://repository.vnu.edu.vn/handle/VNU_123/32538

Synthetic oleananes and seco-oleananes form a group of promising anti-inflammatory and cancer chemopreventive agents with an excellent safety profile.

These compounds are usually prepared by semi-synthesis from natural oleanane triterpenoids.

Since a taraxer-14-ene was reported to be rearranged into an olean-12-ene under mild reaction conditions, a rapid synthesis of seco-oleananes from taraxerone, which is a readily available starting material, was explored by us.

Treatment of taraxerone with m-chloroperoxybenzoic acid gave 14,15-epoxy lactones, which underwent the taraxerane-oleanane rearrangement leading to new seco-oleanane triterpenoids.

Title:

Application of the taraxerane-oleanane rearrangement to the synthesis of seco-oleanane triterpenoids from taraxerone
Authors: Phan, Minh Giang
Vu, Minh Trang
Phan, Tong Son
Keywords: Baeyer-Villiger oxidation
taraxerane-oleanane rearrangement
taraxerone
Issue Date: 2015
Publisher: TAYLOR & FRANCIS LTD, 4 PARK SQUARE, MILTON PARK, ABINGDON OX14 4RN, OXON, ENGLAND
Citation: ISIKNOWLEDGE
Abstract: Synthetic oleananes and seco-oleananes form a group of promising anti-inflammatory and cancer chemopreventive agents with an excellent safety profile. These compounds are usually prepared by semi-synthesis from natural oleanane triterpenoids. Since a taraxer-14-ene was reported to be rearranged into an olean-12-ene under mild reaction conditions, a rapid synthesis of seco-oleananes from taraxerone, which is a readily available starting material, was explored by us. Treatment of taraxerone with m-chloroperoxybenzoic acid gave 14,15-epoxy lactones, which underwent the taraxerane-oleanane rearrangement leading to new seco-oleanane triterpenoids.
Description: NATURAL PRODUCT RESEARCH Volume: 29 Issue: 1 Pages: 64-69 Published: JAN 2 2015 ; TNS05789
URI: http://repository.vnu.edu.vn/handle/VNU_123/32538
ISSN: 1478-6419
Appears in Collections: Bài báo của ĐHQGHN trong Web of Science

 

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