Issue 22, 2010

Stereoselective synthesis of epi-jasmonic acid, tuberonic acid, and 12-oxo-PDA

Abstract

epi-Jasmonic acid (epi-JA) and tuberonic acid (TA) were synthesized from the key aldehyde, all cis-2-(2-hydroxy-5-vinylcyclopentyl)acetaldehyde (14), which was in turn prepared stereoselectively from the (1R)-acetate of 4-cyclopentene-1,3-diol (10) through SN2-type allylic substitution with CH2[double bond, length as m-dash]CHMgBr followed by Mitsunobu inversion, EschenmoserClaisen rearrangement, and regioselective Swern oxidation of the corresponding bis-TES ether (13). Wittig reaction of the aldehyde 14 with [Ph3P(CH2)Me]+Br followed by oxidation afforded epi-JA (3) stereoselectivity over the trans isomer. Similarly, TA (5) was synthesized. Furthermore, the above findings were applied successfully to improve the total efficiency of the previous synthesis of 12-oxo-PDA (1).

Graphical abstract: Stereoselective synthesis of epi-jasmonic acid, tuberonic acid, and 12-oxo-PDA

Supplementary files

Article information

Article type
Paper
Submitted
06 Jun 2010
Accepted
06 Aug 2010
First published
16 Sep 2010

Org. Biomol. Chem., 2010,8, 5212-5223

Stereoselective synthesis of epi-jasmonic acid, tuberonic acid, and 12-oxo-PDA

H. Nonaka, N. Ogawa, N. Maeda, Y. Wang and Y. Kobayashi, Org. Biomol. Chem., 2010, 8, 5212 DOI: 10.1039/C0OB00218F

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