Issue 3, 1996
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Improved synthesis of brassinolide

Trevor C. McMorris,   Rodrigo G. Chavez  and  Prakash A. Patil  

Abstract

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 24S stereochemistry in an intermediate which is readily transformed into brassinolide.

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Article information

DOI
https://doi.org/10.1039/P19960000295
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1996, 295-302

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Improved synthesis of brassinolide

T. C. McMorris, R. G. Chavez and P. A. Patil, J. Chem. Soc., Perkin Trans. 1, 1996, 295 DOI: 10.1039/P19960000295

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