Chemoselective cross metathesis of bishomoallylic alcohols: Rapid access to fragment A of the cryptophycins

Organic Letters

Volumn 6, Issue 12, 2004, Pages 1883-1886

  Lautens, Mark ^a   Maddess, Matthew L ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALKANE DERIVATIVE; CRYPTOPHYCIN DERIVATIVE;

ALLYLATION; ARTICLE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; QUANTUM YIELD; RING CLOSING METATHESIS;

EID: 3042833046     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049883f     Document Type: Article

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32. The formation of styrene was used to measure the progress of RCM since it was the only consistently resolved signal for all the compounds studied.
33. Full results are included in Supporting Information.
34. Authentic samples of the CM products were prepared using conventional reaction conditions to facilitate the kinetic studies. These results are presented in Supporting Information.
35. The yield improved steadily as the amount of coupling partner was increased up to a maximum at 13 equiv relative to the starting material. Higher loadings were not beneficial.
36. Unless otherwise noted the material balance for the results in Table 1 consisted of small amounts of starting material, variable amounts of the RCM product (volatile), and small amounts of RCM/ring-opening metathesis CM products.