1. Efficient and selective synthesis of (S,R,R,S,R,S)-4,6,8,10,16,18-hexamethyl-docosane via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction)
Gangguo Zhu, Bo Liang, Ei-ichi Negishi Org Lett. 2008 Mar 20;10(6):1099-101. doi: 10.1021/ol703056u. Epub 2008 Feb 15.
(S,R,R,S,R,S)-4,6,8,10,16,18-Hexamethyldocosane (1) was synthesized in 11% yield in 11 steps in the longest linear sequence from > or =98% pure (S)-beta-citronellal and 6 additional steps for the preparation of 11 in 23% yield from propene. Five of the six asymmetric carbon centers were generated catalytically and stereoselectively by the ZACA reaction (5 times), one lipase-catalyzed acetylation, and two chromatographic operations.
2. Synthesis of (S,R,R,S,R,S)-4,6,8,10,16,18- hexamethyldocosane from Antitrogus parvulus via diastereoselective hydrogenations
Jianguang Zhou, Ye Zhu, Kevin Burgess Org Lett. 2007 Mar 29;9(7):1391-3. doi: 10.1021/ol070298z. Epub 2007 Mar 6.
[structure: see text]. The hydrocarbon 1 was prepared via a series of catalyst-controlled diastereoselective hydrogenations beginning with fragments derived from the Roche ester.
