201854-68-4

Upstream product

• 201854-74-2 (E)-(4S,5R,6R,7R)-5-(4-Methoxy-benzyloxy)-4,6-dimethyl-7-triethylsilanyloxy-deca-2,9-dienoic acid ethyl ester 
• 201854-75-3 (E)-(4S,5R,6R,7R)-5-(4-Methoxy-benzyloxy)-4,6-dimethyl-7-triethylsilanyloxy-deca-2,9-dien-1-ol 
• 201854-72-0 Benzoic acid (2S,3R,4S,5R)-5-hydroxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-oct-7-enyl ester 
• 201854-73-1 (2S,3R,4R,5R)-3-(4-Methoxy-benzyloxy)-2,4-dimethyl-5-triethylsilanyloxy-oct-7-en-1-ol 
• 201854-71-9 Benzoic acid (2S,3R,4R)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-5-oxo-pentyl ester 
• 201854-70-8 Benzoic acid (2S,3S,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-enyl ester 
• 657389-50-9 3-((4-methoxybenzyl)oxy)-2,4-dimethylhex-5-enal 
• 106357-24-8 (3S,4S,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene 
• 201854-76-4 (2S,3S,4R,5R,6S,7R)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-2,3-epoxy-7-triethyl-silanyloxy-9-decene-1-ol 

Downstream Products

• 552850-11-0 C₅₅H₉₀BrNO₁₁Si₂ 
• 552850-01-8 C₅₃H₈₄BrNO₁₀Si₂ 
• 552850-00-7 6-[9-bromo-1-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-3-methyl-nona-2,4,8-trienyl]-2-(4-{2-[6-(2,2-dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-oxazol-2-ylmethyl)-4-methoxy-tetrahydro-pyran-2-ol 
• 552849-99-7 4-{(E)-2-[(2R,3R,4S,5S,6R)-6-(2,2-Dimethoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydro-pyran-2-yl]-propenyl}-2-methyl-oxazole 
• 552849-97-5 (2R,3R,4R,5R,6R)-2-(2-dimethoxyethylacetal)-6-(1-oxoethyl)-4-(4-methoxy-benzyloxy)-3,5-dimethyltetrahydropyran 

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. A concise stereoselective synthesis of the C20-C26 pentasubstituted oxane ring unit

A stereoselective synthesis of the 2,6-cis oxane unit, accommodating five contiguous asymmetric centres, found in the novel marine natural product phorboxazole A 1, is described.