Determination of the relative and absolute configuration of the dimethylmyristoyl side chain of pneumocandin B0 by asymmetric synthesis.
[reaction: see text] The relative and absolute configuration of the pneumocandin B(0) side chain has been established as (10R,12S)-dimethylmyristoyl by the stereocontrolled synthesis of both antipodes of the side chain acid and their comparison to a sample derived from the natural product.
Leonard
William R
WR
Department of Process Research, Merck Research Laboratories, Merck & Co., P.O. Box 2000, Rahway, New Jersey 07065, USA. bill_leonard@merck.com
Belyk
Kevin M
KM
Bender
Dean R
DR
Conlon
David A
DA
Hughes
David L
DL
Reider
Paul J
PJ
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D054714:Echinocandins; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D010455:Peptides; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D054714:Echinocandins; D010455:Peptides; D010456:Peptides, Cyclic; C079465:pneumocandin B(0)