2294-61-3

Usage

InChI:InChI=1/C12H14O2/c1-2-3-4-5-6-9-12-11(13)8-7-10-14-12/h6,9,11-13H,7-8,10H2,1H3/b9-6+/t11-,12+/m1/s1

Upstream product

• 362675-47-6 (2S,3R)-(-)-3-(tert-butyldimethylsiloxy)-2-[(E)-2-iodovinyl]tetrahydropyran 
• 362675-46-5 (2S,3R)-(-)-3-(tert-butyldimethylsiloxy)-2-ethynyltetrahydropyran 
• 362675-52-3 (2S,3R)-(-)-3-(tert-butyldimethylsiloxy)-2-[(1E)-non-3,5,7-triyn-1-enyl]tetrahydropyran 

Downstream Products

• 692-94-4 (E)-Dec-2-ene-4,6,8-triynoic acid methyl ester 

Relevant academic research and scientific papers

First total synthesis of (-)-ichthyothereol and its acetate

The first and stereoselective total syntheses of (-)-ichthyothereol (1) and its acetate ((+)-2) were achieved by incorporation of the two chiral centers of diethyl L-tartrate. The starting diethyl L-tartrate was converted into trans-2-ethynyl-3-hydroxytetrahydropyran 14 in a stereoselective manner via the endo mode cyclization of the epoxy-alkyne derivative 12. The alcohol 12 was then transformed into (E)-iodoolefin derivative 15, which was exposed to a coupling reaction with 1-tributylstannyl-1,3,5-heptyne (19), derived from the corresponding 1-trimethylsilyl-1,3,5-heptyne (18), under Stille conditions to produce the all-carbon framework of the target natural products. Chemical modification of the coupled product 20 under conventional conditions completed the first total synthesis of (-)-ichthyothereol (1) and its acetate ((+)-2).