A convergent approach to the marine natural product eleutherobin: synthesis of key intermediates and attempts to produce the basic skeleton.
Synthesis of (1R,5R,6R)-2-(6-hydroxymethyl-5-isopropyl-2-methylcyclohex-2-enyl)-N- methoxy-N-methylacetamide 8 from R-(-)-phellandrene in six steps, and (3aR*,4S*,6R*,6aS*)- (6-hydroxymethyl-4-methoxy-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]dioxol- 4-yl)acetic acid methyl ester 17 from tetrabromoacetone and 2-methoxy-5-methylfuran in six steps, provided two key fragments which have been combined to produce intermediates for attempted construction of the basic skeleton of eleutherobin.
Scalabrino
Gaia
G
School of Chemistry, Queen's University Belfast, Belfast BT9 5AG, Northern Ireland, UK.
Sun
Xiao-Wen
XW
Mann
John
J
Baron
Anne
A
D000081:Acetamides / Q000138:chemical synthesis; D000085:Acetates / Q000138:chemical synthesis; D000818:Animals; D037421:Anthozoa / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000081:Acetamides; D000085:Acetates; D004224:Diterpenes; C109551:eleutherobin; C046923:methyl acetate