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Synthesis 2003(3): 0426-0430
DOI: 10.1055/s-2003-37346
PAPER
© Georg Thieme Verlag Stuttgart · New York

New Route for the Synthesis of (22S,23S)-28-Homobrassinolide

Archna P. Massey, Vandana S. Pore, Braja G. Hazra*
Organic Chemistry Synthesis Division, National Chemical Laboratory, Pune - 411 008, India
Fax: +91(20)5893153; e-Mail: hazra@ems.ncl.res.in;
Further Information

Publication History

Received 16 September 2002
Publication Date:
19 February 2003 (online)

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Abstract

A new and highly efficient synthesis of (22S,23S)-28-homobrassinolide (3) has been achieved. (2α,3α,22S,23S)-Tetrahydroxy-5α-stigmastan-6-one (4), a key intermediate for the synthesis of 3, and (2α,3α)-dihydroxy-5α-stigmast-22-en-6-one (6), a versatile intermediate for the synthesis of 3, and several naturally occurring brassinosteroids have been obtained in excellent yield from stigmasta-2,(22E)-dien-6-one (5) by catalytic RuO4 hydroxylation. Sodium perborate, a cheap and large-scale industrial chemical is used for Baeyer-Villiger oxidation of B-ring ketone 9 to its lactone 10.

Key words

brassinosteroids - dihydroxylation - plant growth promoters - ruthenium tetroxide - sodium perborate

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Godrej Agrovet Ltd. Mumbai, India, has commercialised (22S,23S)-homobrassinolide for the enhancement of yields of paddy, wheat, tomato, cabbage, cauliflower, potato, groundnut (peanut), cotton, grapes and tea.