ISSN:
1434-193X
Keywords:
Aplykurodins
;
Marine steroids
;
C-C coupling
;
Cyclic peroxides
;
Lactonization
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
---An approach to the synthesis of aplykurodins, ichthyotoxic marine lactones, is presented. The carbon framework was derived from vitamin D3 by conversion of the readily accessible allyl alcohol 13 to the protected Grundmann's hydroxy ketone 22 and subsequent introduction of the C2 side chain through a Pd0-promoted coupling. Highly stereoselective hetero Diels-Alder reaction with O21 produced the key intermediate peroxide 25. Functional group transformations, coupled with a series of chemo- and stereoselective reactions, finally resulted in the synthesis of the unnatural analogue 17,18-dihydro-3,9-di-epi-aplykurodinone B (6).
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
