370884-72-3

Upstream product

• 370884-69-8 4-[(4aR,5aS,8R,9S,10aR,11aS)-8-(4-Methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-4,4a,5a,6,7,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester 
• 440333-90-4 Trifluoro-methanesulfonic acid (4aR,5aS,8R,9S,10aR,11aS)-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-4,4a,5a,6,7,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl ester 
• 370884-88-1 3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepane 
• 730240-89-8 4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid 
• 370884-49-4 (2R,4aR,9aS)-4a-Methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene-6-carboxylic acid methyl ester 
• 370884-78-9 4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester 
• 370884-82-5 ((2R,4aR,9aS)-4a-Methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl)-methanol 
• 370884-48-3 (2R,4aR,9aS)-4a-Methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-one 
• 439265-00-6 Trifluoro-methanesulfonic acid (2R,4aR,9aS)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl ester 
• 250226-93-8 (E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester 
• 824-94-2 p-methoxybenzyl chloride 
• 116237-17-3 4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester 
• 440333-91-5 4-[(2S,4aR,5aS,8R,9S,10aR,11aS)-8-(4-Methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-3-oxo-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester 
• 370884-71-2 4-[(2S,3R,4aR,5aS,8R,9S,10aR,11aS)-3-Hydroxy-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester 

Downstream Products

• 440333-92-6 4-[(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-3-Hydroxy-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid 
• 370884-73-4 4-[(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-3-Hydroxy-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester 

Relevant academic research and scientific papers

Syntheses of the AB and EFGH ring segments of gambierol

Stereocontrolled syntheses of the AB and EFGH ring systems of gambierol (1) are described. The two key intermediates 3 and 55, representing the AB and EFGH ring frameworks, were prepared from 2-deoxy-D-ribose via linear sequences. Brown's asymmetric allylboration and the intramolecular hetero-Michael reaction were successfully applied to the construction of the A ring moiety. Synthesis of the EFGH ring segment 55 was achieved by the SmI2 mediated reductive cyclization, constructing the EF ring bearing two 1,3-diaxial methyl groups, and the palladium catalyzed coupling of enol triflate and zinc bishomoenolate, making the GH ring moiety. Attempted convergent approaches toward the EFGH ring framework are also described.

Synthetic studies towards gambierol. Part 2: Synthesis of the EFGH ring segment

The EFGH ring segment of gambierol was synthesized from 2-deoxy-D-ribose in 40 steps. The present synthesis includes a SmI2-mediated reductive cyclization and a Pd-catalyzed coupling of enol triflate with a zinc bis-homoenolate as key steps.