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Issue 22, 2010
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Stereoselective synthesis of epi-jasmonic acid, tuberonic acid, and 12-oxo-PDA

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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

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Publication details

The article was received on 06 Jun 2010, accepted on 06 Aug 2010 and first published on 16 Sep 2010


Article type: Paper
DOI: 10.1039/C0OB00218F
Org. Biomol. Chem., 2010,8, 5212-5223

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    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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