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Stereocontrolled (E,Z and erythro, threo) synthesis of ⊙-hydroxyallylic sulphides

✍ Scribed by Andrew B. McElroy; Stuart Warren

Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
165 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis

All four isomers of substituted 3-alkylthio-4-hydroxybutenes have been synthesised:

both the geometry of the double bond and the relative stereochemistry of the two chiral centres are controlled.

We have recently reported' the synthesis of the unstable allylic sulphide (4) via a three stage allylic transposition of the stable allylic phosphine oxide (1). We now report the application of similar reactions to the synthesis of the leukotriene D4 models ( 17), ( 18), ( 26), and ( 28) with stereochemical control over the two chiral centres and the geometry of the double bond. MCPBA 91% PhSLi , THF k Ph2P-p 8 NaH,THF 89% */ f 79 % '?Ph -0 (3) sPh (L)

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