Abstract
An example of the Julia-Lythgoe attachment of the vitamin D side chain to a solid-phase linked Inhoffen-Lythgoe diol derived CD-ring fragment is reported.
Highlights
The development of analogs of 1α,25-dihydroxyvitamin D3 (1, 1α,25(OH)2D3, calcitriol), the hormonally active metabolite of vitamin D3 [1], is an attractive area for organic synthesis [2], ever since it was discovered that structural modifications could lead to derivatives featuring a dissociation between the classical calcemic and antiproliferative/cell-differentiating activities [3]
In the context of developing structural analogs of calcitriol featuring modifications in the side chain, we investigated the possibility of side-chain attachment using the recently described Julia–Lythgoe olefination on solid support [9]
As a first step towards the construction of a vitamin D library following this scenario, we describe the synthesis of 6 in which the C22–C23 connection is realised via Julia–Lythgoe olefination on solid support (Scheme 1)
Summary
The development of analogs of 1α,25-dihydroxyvitamin D3 (1, 1α,25(OH)2D3, calcitriol), the hormonally active metabolite of vitamin D3 [1], is an attractive area for organic synthesis [2], ever since it was discovered that structural modifications could lead to derivatives featuring a dissociation between the classical calcemic and antiproliferative/cell-differentiating activities [3]. Abstract: An example of the Julia–Lythgoe attachment of the vitamin D side chain to a solid-phase linked Inhoffen–Lythgoe diol derived CD-ring fragment is reported.
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