180866-32-4

Upstream product

• 24850-33-7 allyltributylstanane 
• 180866-33-5 (4E,6E)-10-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-deca-4,6-dienal 
• 85116-38-7 (+)-diisopinocampheylallylborane 
• 497-03-0 2-methylbut-2-enal 
• 91266-03-4 tert-butyl-pent-4-ynyloxy-diphenyl-silane 
• 180866-29-9 (2E,5E)-9-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-nona-2,5-dien-4-one 
• 180866-28-8 (2E,5E)-9-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-nona-2,5-dien-4-ol 
• 180866-30-2 Trifluoro-methanesulfonic acid (E)-6-(tert-butyl-diphenyl-silanyloxy)-1-[1-methyl-prop-2-en-(Z)-ylidene]-hex-2-enyl ester 
• 153361-01-4 6-(tert-butyl(diphenyl)silanyloxy)-hex-2-enal 
• 182953-78-2 (4E,6E)-2-Benzenesulfonyl-10-(tert-butyl-diphenyl-silanyloxy)-4-methyl-deca-4,6-dienenitrile 
• 182953-77-1 (2E,4E)-8-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-octa-2,4-dienoic acid ethyl ester 
• 182953-79-3 (4E,6E)-10-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-deca-4,6-dienenitrile 
• 180866-31-3 tert-Butyl-((4E,6E)-7-methyl-nona-4,6,8-trienyloxy)-diphenyl-silane 

Downstream Products

• 155233-30-0 curacin A 
• 180866-34-6 tert-Butyl-((4E,6E)-(R)-10-methoxy-7-methyl-trideca-4,6,12-trienyloxy)-diphenyl-silane 

Relevant academic research and scientific papers

Total synthesis of the antimitotic marine natural product (+)-curacin A

The structurally novel antimitotic agent curacin A was prepared in 15 steps and in 2.6% yield for the longest linear sequence. Key steps in our synthesis are the use of a hydrozirconation-transmetalation protocol for the preparation of divinyl alcohol 8, the stereoselective formation of the acyclic triene segment 11 via enol triflate chemistry, and a second hydrozirconation of the conjugated triene followed by an isocyanide insertion. For the preparation of the heterocyclic moiety of curacin A, the oxazoline → thiazoline conversion offered an efficient access to the sensitive marine natural product.

Synthesis of curacin A, an antimitotic cyclopropane-thiazoline from the marine cyanobacterium Lyngbya majuscula

Charette asymmetric cyclopropanation, chiral thiazoline synthesis by thioamide cyclization under modified Mitsunobu conditions, Ti(iPrO)4/bi-naphthol catalyzed allylstannane addition, and an exceptionally mild two-carbon homologation via dehydrative alkylation with phenylsulfonylacetonitrile/Ph3P/ADDP convened in an efficient, stereocontrolled route to the title bioactive heterocycle.