1.
J Nat Prod
; 80(8): 2335-2344, 2017 08 25.
Article
in English
| MEDLINE
| ID: mdl-28767241
ABSTRACT
The originally proposed structure of astakolactin was revised, and an asymmetric total synthesis of the newly proposed structure was achieved. The key transformations in the synthesis were a Johnson-Claisen rearrangement, an asymmetric Mukaiyama aldol reaction, and a Mitsunobu-type cyclodehydration. The spectroscopic data and specific rotation of the compound obtained matched well with those reported for naturally occurring astakolactin.
Subject(s)
Aldehydes/chemistry , Terpenes/chemical synthesis , Molecular Structure , Stereoisomerism , Terpenes/chemistry
2.
Beilstein J Org Chem
; 10: 2421-7, 2014.
Article
in English
| MEDLINE
| ID: mdl-25383112
ABSTRACT
The first total synthesis of the proposed structure of astakolactin, a sesterterpene metabolite isolated from the marine sponge Cacospongia scalaris, has been achieved, mainly featuring Johnson-Claisen rearrangement, asymmetric Mukaiyama aldol reaction and MNBA-mediated lactonization.