A practical convergent route to (23S,25R)-1α,25-dihydroxyvitamin D326,23-lactone
- 1 January 1992
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 17,p. 1229-1231
- https://doi.org/10.1039/c39920001229
Abstract
The Ireland–Claisen rearrangement of the lactate 8, prepared from the Inhoffen–Lythgoe diol 5, followed by iodolactonisation allowed easy access to the C–D-ring fragment 4, from which a novel convergent synthesis of (23S,25R)-1α,25-dihydroxyvitamin D3 26,23-lactone 1 has been accomplished via coupling with the A-ring fragment 3.Keywords
This publication has 17 references indexed in Scilit:
- Facile stereoselective synthesis of (23S,25R)-1.alpha.,25-dihydroxyvitamin D3 26,23-lactone, a major metabolite of 1.alpha.,25-dihydroxyvitamin D3The Journal of Organic Chemistry, 1992
- A novel convergent synthesis of (+)-1.alpha.,25-dihydroxyvitamin D3 using a chromium(II)-mediated coupling reactionThe Journal of Organic Chemistry, 1991
- Effects of diastereoisomers of 1,25-dihydroxyvitamin D3-26,23-lactone on alkaline phosphatase and collagen synthesis in osteoblastic cellsMolecular and Cellular Endocrinology, 1988
- The stereochemical configuration of the natural 1α,25-dihydroxyvitamin D3-26,23-lactoneArchives of Biochemistry and Biophysics, 1985
- A highly stereoselective route to calcitriol lactoneThe Journal of Organic Chemistry, 1985
- The unique action for bone metabolism of 1α,25-(OH)2D3-26,23-lactoneBiochemical and Biophysical Research Communications, 1985
- Total synthesis of 1.alpha.,25(R)-dihydroxy vitamin D3 26, 23(S)-lactone (calcitriol lactone), a natural metabolite of vitamin D3The Journal of Organic Chemistry, 1983
- Role of kidney tissue in the production of 25-hydroxyvitamin D3-26,23-lactone and 1 alpha, 25-dihydroxyvitamin D3-26,23-lactone.Proceedings of the National Academy of Sciences, 1980
- Isolation of a new metabolite of vitamin D produced in vivo, 1α,25-dihydroxyvitamin D3-26,23-lactoneArchives of Biochemistry and Biophysics, 1980
- Simonsen Lecture. Synthetic approaches to vitamin D and its relativesChemical Society Reviews, 1980