265666-16-8

Upstream product

• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 265666-29-3 (4S,1'R,3'R)-4-[3'-hydroxy-1'-(triethylsilanyloxy)-hex-5'-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Downstream Products

• 657389-56-5 4-((2R,4R,6R)-6-{(2R,6R)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-pyran-2-ylmethyl}-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-2-(4-methoxy-benzyloxymethyl)-oxazole 
• 657389-92-9 Methanesulfonic acid 3-((R)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-1-{(2S,4R,6R)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enyl ester 
• 265666-25-9 (2'S,4'R,6'R,5R)-methanesulfonic acid 5,7-dihydroxy-1-{6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl-methyl}-3-methyleneheptyl ester 
• 265666-24-8 (2'R,4'R,6'R,4''R)-4-(2'',2''-dimethyl-[1'',3'']-dioxan-4''-ylmethyl)-1-{6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl}-pent-4-en-2-ol 
• 265666-12-4 (2'R,4'R,6'R,2R,6R)-2''-({6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl-methyl}-4-methylene-tetrahydropyran-2-yl)-ethanol 
• 265666-18-0 (1S,2'S,4'R,6'R)-[6'-{2-hydroxy-1-[2-(4-methoxybenzyloxy)-acetylamino]-ethyl}-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-acetic acid ethyl ester 
• 657389-89-4 ((2S,4R,6R)-6-{(R)-1-[2-(4-Methoxy-benzyloxy)-acetylamino]-2-oxo-ethyl}-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-acetic acid ethyl ester 
• 265666-19-1 (2'S,4'R,6'R)-[6'-{2-(4-methoxybenzyloxymethyl)-oxazol-4-yl}-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-acetic acid ethyl ester 
• 265666-21-5 (2'R,4'R,6'R)-3''-{6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl}-propane-1'',2''-diol 
• 265666-22-6 (2'R,4'R,6'R)-2-(4-methoxybenzyloxymethyl)-4-(6'-oxiranylmethyl-4'-triisopropylsilanyloxy-tetrahydropyran-2'-yl)-oxazole 
• 265666-20-4 (2'R,4'R,6'R)-4-(6'-allyl-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl)-2-(4-methoxybenzyloxymethyl)-oxazole 
• 265666-31-7 (2'S,4'R,6'R)-[6'-{2-(4-methoxybenzyloxymethyl)-oxazol-4-yl}-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-acetaldehyde 

Relevant academic research and scientific papers

Total synthesis of (+)-phorboxazole A, a potent cytostatic agent from the sponge Phorbas sp.

A convergent total synthesis of phorboxazole A (1a), from the C(3-19), C(20-27) and C(33-46) fragments 5, 4 and 91, respectively, concentrating on stereocontrolled formation of the bonds at C(2-3), C(19-20) and C(27-28), is described. Although a coupling reaction between a macrolide ketone and the side chain substituted sulfone, at C(27-28) was not successful, a Wadsworth-Emmons olefination involving the oxane methyl ketone 4 and an oxazole produced the oxane 90 which was next coupled to 91 leading to the C(20-46) unit 100. A further coupling of 100 to 71c at C(19-20) then led to 105, ultimately, and the synthesis was completed by a macrocyclisation reaction from 105, at the C(2-3) alkene bond, followed by deprotection of 106.

Synthetic studies towards phorboxazole A. Stereoselective synthesis of the C3-C19 bis-oxane oxazole portion of the phorboxazole macrolide

A synthesis of the C3-C19 bis-oxane portion of phorboxazole A, involving an oxy anion intramolecular Michael reaction to produce a cis-oxane and an intramolecular Williamson reaction leading to a trans-oxane, is described. (C) 2000 Elsevier Science Ltd.