NEW SYNTHETIC APPROACH TO THE WESTERN PART C-10-C-15 OF (+/-)-DES-EPOXY-ROSARAMYCIN

A new route to (5E,7E,3R*,4S*)-4,6-dimethyl-8-tri-n-butylstannyl-octa-5,7-dien-3-ol 5 which represents the western part C-10-C-15 Of the macrocyclic antibiotic (+/-)-des-epoxy-rosaramycin I, was explored. Direct model catalytic palladium coupling reaction between (3E)-4-iodo-pent-3-en-1-ol 8 and (E)...

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Published inSynlett no. 12; pp. 998 - 1000
Main Authors LEMENEZ, P, BERQUE, FARGEAS, ARDISSON, J, PANCRAZI, A
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.12.1994
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HIGHER-ORDER
ENOL ETHERS
COUPLING REACTIONS
TRISUBSTITUTED ALKENES
VINYLSTANNANES
ERYTHRONOLIDE-B
ERYTHROMYCINS
STEREOSELECTIVE SYNTHESIS
GRIGNARD-REAGENTS
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Summary:A new route to (5E,7E,3R*,4S*)-4,6-dimethyl-8-tri-n-butylstannyl-octa-5,7-dien-3-ol 5 which represents the western part C-10-C-15 Of the macrocyclic antibiotic (+/-)-des-epoxy-rosaramycin I, was explored. Direct model catalytic palladium coupling reaction between (3E)-4-iodo-pent-3-en-1-ol 8 and (E)-1,2bis(tri-n-butylstannyl) ethylene gave (3E,5E)-4-methyl-6-tributylstannyl-hex-3,5-dien-1-ol 4 in 36% yield. Stannyl cupration performed on the (5E,3R*,4S*)-4,6-dimethyl-oct-5-en-7-yn-3-ol 15 led in high yield to the expected stannyl diene 5.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-1994-34982