Lite Version|Standard version

To gain access to this content please
Log in via your home Institution.
Log in with your member or subscriber username and password.
Download

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

Page: ^ Top