Application of Conformation Design in Acyclic Stereoselection: Total Synthesis of Borrelidin as the Crystalline Benzene Solvate

Journal of the American Chemical Society

Volumn 125, Issue 45, 2003, Pages 13784-13792

  Hanessian, Stephen ^a   Yang, Yang ^a   Giroux, Simon ^a   Mascitti, Vincent ^a   Ma, Jianguo ^a   Raeppel, Franck ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACYCLIC STEREOSELECTION;

BENZENE; CARBOXYLIC ACIDS; CRYSTAL STRUCTURE; ESTERS; ISOMERS; NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

ANTIBIOTICS;

ALKADIENE; ALLYL COMPOUND; BENZENE DERIVATIVE; BENZYL THIOCYANATE; BORRELIDIN; CARBOXYLIC ACID DERIVATIVE; COPPER DERIVATIVE; CUPRATE; CYANODIENE DERIVATIVE; DEOXYPROPIONATE DERIVATIVE; ESTER DERIVATIVE; GAMMA HYDROXYCYCLOPENTANECARBOXYLIC ACID; GLYCERALDEHYDE; HETEROCYCLIC COMPOUND; MACROLIDE; MALIC ACID; METHYL GROUP; PROPIONIC ACID DERIVATIVE; TREPONEMYCIN; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; CRYSTALLIZATION; CYCLIZATION; DRUG SYNTHESIS; ENERGY; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TECHNIQUE; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; CYCLOPENTANES; FATTY ALCOHOLS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PROPIONIC ACIDS; STEREOISOMERISM;

EID: 0242659004     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030139k     Document Type: Article

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173. For the effect of TMSC1. see (a) Bertz, S. H.; Miao, G.; Rossiter, B. E. ; Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11023.
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176. The corresponding ketene acetals could be isolated by avoiding any acidic workup. See also refs 32a,b.
177. As previously discussed, a fourth cuprate addition to 10 was also synselective but only modestly (syn/anti 4:1), presumably due to entropic limitations of a growing deoxypropionate chain, as observed by Hoffmann.54a
178. 7 anti-deoxypropionate (anti-7), under the same conditions led to a 2:1 mixture of isomers, indicating the preference for a syn-disposed deoxypropionate motif such as 7 for all-syn selectivity.
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