135041-03-1

Upstream product

• 135040-96-9 (1S-cis)-1-ethynyl-2-methylenebicyclo<3.1.0>hexane 
• 135040-95-8 (1S-cis)-1-ethynylbicyclo<3.1.0>hexan-2-one 
• 135040-92-5 <4'R,5'R-(1S-cis)>-(+)-4',5'-dimethylspirohexane-2,2'-<1,3>dioxolane>-1-methanol 
• 135040-99-2 -1-<(trimethylsilyl)ethynyl>bicyclo<3.1.0>hexan-2-ol 
• 135041-01-9 (1R-cis)-trimethyl<(2-methylenebicyclo<3.1.0>hexyl)ethynyl>silane 
• 135040-91-4 (2R,3R)-(-)-2,3-dimethyl-1,4-dioxaspiro<4.4>non-6-ene-6-methanol 
• 135041-00-8 (1S-cis)-1-<(trimethylsilyl)ethynyl>bicyclo<3.1.0>hexan-2-one 
• 135040-94-7 <4'R,5'R-(1S-cis)>-1-ethynyl-4',5'-dimethylspirohexene-2,2'-<1,3>dioxolane> 
• 135040-98-1 (R)-2-<(trimethylsilyl)ethynyl>-2-cyclopenten-1-ol 
• 33948-35-5 2-iodo-cyclopent-2-enone 
• 135040-97-0 (1R)-2-iodocyclopent-2-en-1-ol 
• 145415-23-2 2-iodo-2-cyclopenten-1-ol 
• 135040-93-6 <4'R-<2'α(1S*,5R*),4'α,5β>>-4',5'-dimethylspirohexane-2,2'-<1,3>dioxolane>-1-carboxaldehyde 
• 68882-71-3 2-(hydroxymethyl)cyclopent-2-enone 

Downstream Products

• 135041-04-2 <1R-<1α(R*),3aβ,4α(1S*,3S*,5S*),7aα>>-4-<<3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-2-methylenebicyclo<3.1.0>hexan-1-yl>ethynyl>octahydro-7a-methyl-1-<1,5,5-trimethyl-5-((trimethylsilyl)oxy)pentyl>-1H-inden-4-ol 
• 32222-06-3 calcitriol 
• 135041-05-3 <1R-<1α(R*),3aβ,4α<(E)-(1S*,3S*,5R*)>,7aα>>-1-<1,5-dimethyl-5-<(trimethylsilyl)oxy>hexyl>-4-<2-<3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-2-methylenebicyclo<3.1.0>hexan-1-yl>ethenyl>octahydro-7a-methyl-1H-inden-4-ol 

Relevant academic research and scientific papers

Control of stereoselectivity in samarium metal induced cyclopropanations. Synthesis of 1,25-Dihydroxycholecalciferol

1,25-Dihydroxycholecalciferol (23) was synthesized from A-ring precursor 18 and Windaus-Grundmann ketone 19 via cyclovitamin D 21. Key reactions include highly stereoselective (5 to 6) and stereospecific (13 to 14) cyclopropanations.

Convergent synthesis of vitamin D3 metabolites. Control of the stereoselectivity in samarium-induced cyclopropanations of cyclopentenes

The 25-hydroxy and 1α,25-dihydroxy vitamin D3 metabolites are obtained by solvolytic rearrangements of the 1-desoxy and 1α-hydroxy cyclopropyl vinylogous alcohols 31 and 29, respectively, with simultaneous formation of the vitamin D structural triene and the 3-hydroxy function. Two complementary methods have been employed to direct the stereoselectivity of the samarium induced olefin cyclopropanations which ultimately lead to key chiral ring A precursors. One protocol uses the two stereogenic centers of the (R,R)-2,3-butanediol ketal moiety of 8, while the other method uses the allylic hydroxyl group of (R)-16.