Stereocontrolled Synthesis of a Nonracemic Vitamin B12 A−B-Semicorrin

Mulzer, Johann; List, Benjamin; Bats, Jan W.

doi:10.1021/ja9700515

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Stereocontrolled Synthesis of a Nonracemic Vitamin B₁₂ A−B-Semicorrin

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Mulzer, J., List, B., & Bats, J. W. (1997). Stereocontrolled Synthesis of a Nonracemic Vitamin B₁₂ A−B-Semicorrin. Journal of the American Chemical Society, 119(24), 5512-5518. doi:10.1021/ja9700515.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-A50A-B

Abstract

The first synthesis of a vitamin B₁₂ A−B-semicorrin 44 is described. Both A and B rings were prepared from the same precursor, enamide 40, which is obtained by a sequence of sigmatropic rearrangements and a biomimetic oxylactonization. The coupling has been achieved via Eschenmoser sulfide contraction. A−B-semicorrin 44 allows a new approach toward vitamin B₁₂ and other uroporphinoids.