Journal of Organic Chemistry p. 2135 - 2139 (1991)
Update date:2022-08-04
Topics:
Casiraghi, Giovanni
Colombo, Lino
Rassu, Gloria
Spanu, Pietro
Enantiomerically pure undecose acetonide 9 was synthesized, through heptose intermediate 5, starting with D-glyceraldehyde acetonide (1).The key steps were two consecutive four-carbon homologations, each consisting of four reactions: (i) stereoselective elongation of the aldehyde precursor with 2-(trimethylsiloxy)furan, giving Cn+4 butenolide templates 2 and 6, (ii) anti-selective cis-dihydroxylation of the butenolide double bond, giving fully functionalized lactones 3 and 7, (iii) lactone ring opening and protection, giving open-chain methyl esters 4 and 8, and (iv) DIBAL reduction to aldoses 5 and 9.At the end of the eight-step sequence, undecose 9 was prepared in a 5.1percent overall yield, which corresponded to a 69.5percent average yield per step.
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