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Synthesis of 6-Hydroxyalkylidenepenicillanates
Synthesis of 6-Hydroxyalkylidenepenicillanates
Journal of the Korean Chemical Society. 1999. Aug, 43(4): 447-455
  • Published : August 00, 1999
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Lee, Jung Hwan
Ko, Jae Young
Seo, Kyung Jae
Goo, Yang Mo
Lee, Youn Young

Abstract
Allyl (5R)-(Z)- and (5R)-(E)-6-[(2S)-2,3-isopropylidenedioxypropylidene]Penicillanate(10a and 10b) were prepared from allyl (5R)-dibromopenicillanate(6) via a sequence of reactions involving condensation with 2,3-O-isopropylidene-D-glyceraldehyde, reduction with $Zn-NH_4OAc$, and Mitsunobu elimination. Deprotection of isopropylidene and allyl groups of 10a gave potassium (5R)-(Z)-6-[(2S)-2,3-dihydroxypropylidene]penicillanate(4). However, deprotection of isopropylidene group of 10b afforded ${\alpha},\;{\beta}$-unsaturated-lactone(12). Allyl (5R)-(Z)- and (5R)-(E)-6-[(2S)-2-(t-butyldimethlsilyloxy)propylidene]penicillanate(18a and 18b) were prepared from ally (5R)-dibromopenicillanate(6) via a sequence of reactions involving condensation with (2S)-2-(t-butyldimethylsilyloxy)propanal(15), reduction with $Zn-NH_4OAc$ and Mitsunobu elimination or mesylation-elimination. Deprotection of t-butyldimethylsilyl and allyl groups of 18a and 18b gave potassium (5R)-(Z)- and (5R)-(E)-6-[(2S)-2-hydroxypropylidene]penicillanate(5a and 5b), respectively.