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Asymmetric Total Synthesis of (11R, 12S, 13S, 9Z, 15Z)-9, 12, 13-Trihydroxyoctadeca-9, 15-dienoic Acid, a self-defensive agent against rice-blast disease

โœ Scribed by Alain Baudat; Pierre Vogel

Publisher
John Wiley and Sons
Year
1994
Tongue
German
Weight
362 KB
Volume
77
Category
Article
ISSN
0018-019X

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โœฆ Synopsis

85 (12)

, 81 (13), 75 (loo), 73 (84). Anal. calc. for CI5H2,O5Si (316.5): C 56.93, H 8.92, Si 8.87; found: C 56.79, H 8.82, Si 8.77.

(I R.2S.3 S,4S)-I-[ ( tert-Butyl)dimethylsilyloxyjtetrahydro-2,3-(isopropylidenedioxy/-4-f ( Z/-pent-T-enyI]furan ((+)-7).

Dropwise, a 15 % (Me,Si),NK soh. in toluene (2.0 ml, 1.32 mmol) was added to a stirred suspension CDCl3): 5.37 (s, H-C(l)); 4.67 (d, 'J = 5.8, H-C(3)); 4.58 (dd, 3J = 8.0, 7.3, H-C(4)); 4.57 (d, ' J = 5.8, H-C(2)); CDCI,): 5.26 (d, 3J =4.1, H-C(1)); 4.62 (dd, ' J = 7.4, 4.1, H-C(2)); 4.54 (dd, ' J = 7.4, 3.7, H-C(3)); 4.46 (ddd, CI-MS(NH~):331(11),315(6),289(8),231 (100),215(35), 199(13), 171 (15), 161 (Il), 157(26), 129(37), 103(35),

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Enantiocontrolled Synthesis of (11S,12S,13S)-(9Z,15Z)-and (11R,12S,13S)-(9Z,15Z)-11-Hydroxy-12,13-epoxy Octadecadienoic Acids by Means of the Sharpless Asymmetric Epoxidation of the Unsymmetrical Divinylcarbinol. -The enantioselective synthesis of the title compounds (V) and (VI), self-defensive su