Total syntheses of racemic and natural glycinol.
Total syntheses of racemic and (-)-glycinol (1) are described. A Wittig reaction produced the isoflav-3-ene from which a Sharpless dihydroxylation introduced either the racemic or enantiomeric 6a-hydroxy group. A 5.5% overall yield of racemic material was obtained after 12 steps. A method was devised for a one-pot switch of protecting groups masking a sensitive resorcinolic para-functionality, and conditions were optimized to prompt spontaneous closure of the pterocarpanolic dihydrofuran upon subsequent exposure of its ortho-functionality. These improvements eliminated two steps and increased the overall yield to 9.8% during production of the natural enantiomer.
Luniwal
Amarjit
A
Center for Drug Design and Development, Department of Medicinal and Biological Chemistry, The University of Toledo College of Pharmacy, Toledo, Ohio 43606-3390, USA.
Khupse
Rahul S
RS
Reese
Michael
M
Fang
Lei
L
Erhardt
Paul W
PW
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D044948:Flavonols / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001688:Biological Products; D044948:Flavonols; C540862:glycinol