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Review
, 148, 31-3

An Efficient Convergent Synthesis of 1α,25-dihydroxy-3-epi-vitamin D2

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Review

An Efficient Convergent Synthesis of 1α,25-dihydroxy-3-epi-vitamin D2

Rita Sigüeiro et al. J Steroid Biochem Mol Biol.

Abstract

The first synthesis of 1α,25-dihydroxy-3-epi-vitamin D2 is described. Key steps of the synthesis entail the construction of the triene unit by a Pd-catalyzed ring closure of an enol-triflate (A-ring fragment) followed by a Suzuki-Miyaura coupling with a boronate (upper fragment), and the installation of the methyl group at C-24 by an SN2'-syn displacement of an allylic carbamate. This article is part of a Special Issue entitled 'SI:17th Vitamin D Workshop'.

Keywords: 1α,25-dihydroxy-3-epi-vitamin D(2); Pd-catalyzed cascades; Vitamin D(2) analogues synthesis.

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