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