A new approach to annelated butenolides. The total synthesis of (±)‐isodrimenin
- 1 January 1987
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 106 (9) , 505-508
- https://doi.org/10.1002/recl.19871060906
Abstract
A new approach to annelated butenolides has been developed starting from trans‐5,5,8a‐trimethyl‐3,4,4a,5,6,7,8,8a‐octahydro‐1(2H)‐naphthalenone (3) and cyclohexanones. A reaction sequence consisting of formylation of the enolates of these ketones, protection of the formyl group as its dioxolane and addition of methoxy(phenylthio)methyllithium has been used to introduce the necessary functionalized carbon atoms. Rearrangement of the adducts to α‐(phenylthio)aldehydes, followed by hydrolysis of the dioxolane, resulted in the formation of butenolides. The method has been demonstrated in the total synthesis of (±)‐isodrimenin. Direct hydrolysis of the adducts, obtained after addition of methoxy(phenylthio)methyllithium, followed by treatment with acid, also gave butenolides.Keywords
This publication has 24 references indexed in Scilit:
- A novel synthesis of α‐(phenylthio)aldehydesRecueil des Travaux Chimiques des Pays-Bas, 1987
- Drimane-type sesqui- and norsesquiterpenoids from polygonum hydropiperPhytochemistry, 1985
- The olefin metathesis/transannular ene sequence: a method for the stereocontrolled synthesis ofTetrahedron Letters, 1982
- Synthesis of euryfuran, valdiviolide, and confertifolinTetrahedron Letters, 1981
- A novel synthesis of α-sulfenylated aldehydesTetrahedron Letters, 1981
- A stereospecific total synthesis of waburganalTetrahedron Letters, 1980
- Stereoselective total syntheses of (±)-warburganal and (±)-isotadeonalTetrahedron Letters, 1980
- Muzigadial and warburganal, potent antifungal antiyeast, and African army worm antifeedant agentsTetrahedron Letters, 1977
- Potent army worm antifeedants from the east African Warburgia plantsJournal of the Chemical Society, Chemical Communications, 1976
- The total synthesis of isoiresin, dihydroiresin, and isodihydroiresinJournal of the American Chemical Society, 1968