Proof of the Structure of the Stemodia chilensis Tetracyclic Diterpenoid (+)-19-Acetoxystemodan-12-ol by Synthesis from (+)-Podocarpic Acid: X-ray Structure Determination of a Key Intermediate
- 3 March 2016
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 79 (4) , 1155-1159
Abstract
The first synthesis of (+)-19-acetoxystemodan-12-ol (1), a stemodane diterpenoid isolated from Stemodia chilensis, is described. The structure was supported by an X-ray crystallographic analysis of intermediate (+)-9a, which confirmed the proposed structure and excluded the structure of (−)-19-hydroxystemod-12-ene as a possible candidate for the Chilean Calceolaria diterpenoid to which the (−)-19-hydroxystemar-13-ene structure (9b) had been erroneously assigned.Keywords
Funding Information
- Ministero dell’Istruzione, dell’Università e della Ricerca (RBFR12BGHO_002)
- Sapienza Università di Roma (000004_14_RDB_BIAN)
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