Volume 21, Issue 7 pp. 893-897

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Studies on the Model Synthesis of the Brassinolide and Dolicholide's Side Chains^†

Li-Zeng Peng,

Li-Zeng Peng

National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China

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Feng-Zhi Zhang,

Feng-Zhi Zhang

National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China

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Tian-Sheng Mei,

Tian-Sheng Mei

National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China

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Tao Zhang,

Tao Zhang

National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China

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Hua-Wei Liu,

Hua-Wei Liu

National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China

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Yu-Lin Li,

Yu-Lin Li

[email protected]

National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China

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Li-Zeng Peng,

Li-Zeng Peng

National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China

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Feng-Zhi Zhang,

Feng-Zhi Zhang

National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China

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Tian-Sheng Mei,

Tian-Sheng Mei

National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China

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Tao Zhang,

Tao Zhang

National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China

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Hua-Wei Liu,

Hua-Wei Liu

National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China

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Yu-Lin Li,

Yu-Lin Li

[email protected]

National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China

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First published: 26 August 2010

https://doi.org/10.1002/cjoc.20030210734

^†

Dedicated to Professor ZHOU Wei-Shan on the occasion of his 80th birthday.

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Abstract

A highly stereoselective synthesis of the side chain enantiomers of brassinolide and dolicholide through an aldol reaction of 2-(4-methoxy benzyloxyl) propionylaldehyde (5) with the anion of 1-(tert-butyldimethylsiloxy)-3-methyl-2-butanone (6) is described.

References and notes

1 Grove, M. D.; Spencer, G. F.; Rohwedder, W. K.; Mandava, N; Worley, J. F.; Warthen, J. D. Jr.; Steffens, G. L.; Flippen-Anderson, J. L.; Cook, J. C. Jr., Nature 1979, 281, 216.
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(b) The stereochemistry at C-3 is predicted by the Cram or Felin-Anh model for the transition state.
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Volume21, Issue7

July 2003

Pages 893-897

Studies on the Model Synthesis of the Brassinolide and Dolicholide's Side Chains^†

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Studies on the Model Synthesis of the Brassinolide and Dolicholide's Side Chains†

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Studies on the Model Synthesis of the Brassinolide and Dolicholide's Side Chains^†