Stereoselective construction of a β-isopropenyl alcohol moiety at the C (2) and (3) of Kallolide A and Pinnatin A using a [2, 3] Wittig rearrangement of cyclic furfuryl …

M Tsubuki, K Takahashi, T Honda

Index: Tsubuki, Masayoshi; Takahashi, Kazunori; Honda, Toshio Journal of Organic Chemistry, 2003 , vol. 68, # 26 p. 10183 - 10186

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Citation Number: 24

Abstract

A stereocontrolled synthesis of anti-and syn-β-isopropenyl alcohol moieties at the C (2)-C (3) positions of kallolide A and pinnatin A was accomplished employing the [2, 3] Wittig rearrangement of (E)-and (Z)-cyclic furfuryl ethers 8. Enantioselective Wittig rearrangement of (E)-and (Z)-furfuryl ethers 8 using butyllithium and a chiral bis (oxazoline) was also examined to provide (2 R, 3 R)-homoallylic alcohol anti-9 in up to 61% ee and (2 R, 3 S)- ...