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480-49-9

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Total synthesis of Filipin III
Filipin III (1), a polyene macrolide antibiotic, has been synthesized for the first time. The polyol chain was assembled using a stereoselective carbon-carbon bond forming strategy previously developed in our lab: a cyanohydrin acetonide alkylation and reductive decyanation sequence. The polyene segment was prepared from L-ascorbic acid. These two components were coupled using Yamaguchi's esterification, and cyclized with an intramolecular Horner-Emmons reaction to form a trisubstituted alkene. Stereoselective reduction followed by deprotection gave filipin III. This highly convergent approach to filipin III represents the first total synthesis of a methylpentaene macrolide antibiotic.
Richardson, Timothy I.,Rychnovsky, Scott D.
p. 8977 - 8996
(2007/10/03)

Total Synthesis of Filipin III
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Richardson, Timothy I.,Rychnovsky, Scott D.
p. 12360 - 12361
(2007/10/03)

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165329-49-7
1',3:5,7:9,11:13,15-tetrakis-O-(1-methylethylidene)filipin III

Chemical Properties

Melting Point: 163-180° (Bergy, Eble)
Boiling Point: 913.9 °C at 760 mmHg
Flash Point:279.3 °C
Density: 1.161 g/cm³
Solubility:Soluble in Methanol (up to 10 mg/ml)
Storage Temp.:−20°C
Vapor Pressure: 0mmHg at 25°C
Refractive Index: 1.535
PKA: 12.77±0.70(Predicted)
PSA: 208.37000
LogP: 1.88800

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