Total synthesis of (+)-wailupemycin B

Angewandte Chemie - International Edition

Volumn 42, Issue 38, 2003, Pages 4685-4687

  Kirsch, Stefan ^a   Bach, Thorsten ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Antibiotics; Asymmetric synthesis; Ketones; Polyketides; Total synthesis

Indexed keywords

ALCOHOLS; OXIDATION;

ORTHOGONAL PROTECTING GROUPS;

SYNTHESIS (CHEMICAL);

ALCOHOL; CARVONE; CYCLOHEXANONE DERIVATIVE; FUNCTIONAL GROUP; KETONE; POLYKETIDE; UNCLASSIFIED DRUG; WAILUPEMYCIN B;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; DEPROTECTION REACTION; OXIDATION; STEREOCHEMISTRY;

CYCLOHEXANONES; MOLECULAR STRUCTURE; PYRONES; STREPTOMYCES;

EID: 0142056062     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351455     Document Type: Article

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34. The relative configurations and conformations of various intermediates were been determined throughout the synthesis by NOESY experiments. The rigid precursor to compound 2, which already contains all stereogenic centers of the natural product, offered a chance to check the relative configuration. The most important NOE data (-=medium,-= strong) are given in the illustration (Ar=4-methoxy-6-oxopyran-2-yl).
35. +], 356 (48), 209 (51), 140 (100), 125 (50), 105 (92), 77 (33).