Journal of the Chemical Society. Perkin transactions I p. 295 - 302 (1996)
Update date:2022-08-03
Topics:
McMorris, Trevor C.
Chavez, Rodrigo G.
Patil, Prakash A.
Brassinolide has been synthesized from stigmasterol in an overall yield of 7%. The key step in the synthesis is aldol condensation of 2α,3α-isopropylidenedioxy-6-oxo-23,24-dinor-5α-cholan-22-al with 3-isopropylbut-2-enolide carried out at -78°C, which gives a product with 22R,23R stereochemistry in high yield. Catalytic hydrogenation of this product is highly stereoselective leading to the desired 245 stereochemistry in an intermediate which is readily transformed into brassinolide. Copyright 1996 by the Royal Society of Chemistry.
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