120040-85-9

Upstream product

• 120040-82-6 methyl (E)-(4S,5R,6S,7S)-5-acetoxy-7-(benzyloxy)-9,9-dibromo-2,4,6-trimethylnona-2,8-dienoate 
• 146517-98-8 (E)-(4R,5S,6S,7S)-5-Acetoxy-7-benzyloxy-8,9-dihydroxy-2,4,6-trimethyl-non-2-enoic acid methyl ester 
• 120040-80-4 (E)-(4R,5S,6S,7S)-5-Acetoxy-7-benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4,6-trimethyl-hept-2-enoic acid methyl ester 
• 120040-79-1 (E)-(4R,5S,6S,7S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-2,4,6-trimethyl-hept-2-enoic acid methyl ester 
• 120040-78-0 (1S,2S,3S,4R)-1-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,4-dimethyl-hex-5-en-3-ol 
• 146518-09-4 (2S,3R,4S,5S)-5-Benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2,4-dimethyl-pentanal 
• 120040-78-0 (3S,4R,5S,6S,7S)-6-(benzyloxy)-3,5-dimethyl-4-hydroxy-7,8-(isopropylidenedioxy)oct-1-ene 
• 120143-05-7 (3S,4S,5S)-4-(benzyloxy)-5,6-(isopropylidenedioxy)-3-methylhex-1-ene 
• 120040-84-8 methyl (E,Z,E,E)-(4S,5R,6S,7S)-5-acetoxy-7-(benzyloxy)-9-bromo-14-hydroxy-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate 
• 146517-98-8 methyl (E)-(4S,5R,6S,7S,8S)-5-acetoxy-7-(benzyloxy)-8,9-dihydroxy-2,4,6-trimethylnon-2-enoate 
• 120040-80-4 methyl (E)-(4S,5R,6S,7S,8S)-5-acetoxy-7-(benzyloxy)-8,9-(isopropylidenedioxy)-2,4,6-trimethylnon-2-enoate 
• 146517-99-9 (E)-(4R,5S,6S,7S)-5-Acetoxy-7-benzyloxy-2,4,6-trimethyl-8-oxo-oct-2-enoic acid methyl ester 
• 120040-79-1 methyl (E)-(4S,5R,6S,7S,8S)-7-(benzyloxy)-5-hydroxy-8,9-(isopropylidenedioxy)-2,4,6-trimethylnon-2-enoate 
• 120040-77-9 (2R,3S)-3-Benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde 

Downstream Products

• 120040-88-2 methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate 
• 120040-87-1 methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate 
• 146518-11-8 (1S,2S,4aS,5R,6R,7S,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-(imidazole-1-carbothioyloxy)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 120040-86-0 methyl 2β-<(E)-3-hydroxy-1-methylprop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate 
• 120040-86-0 (1S,2S,5R,6S,7S,8R,8aR)-5-Benzyloxy-7-hydroxy-2-((E)-3-hydroxy-1-methyl-propenyl)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Application of the steric directing group strategy to the stereoselective synthesis of the octahydronaphthalene substructure of kijanolide and tetronolide

A highly stereoselective synthesis of the kijanolide/tetronolide octahydronaphthalene substructure 4 has been completed. The synthesis proceeds in 16 steps from L-glyceraldehyde acetonide (8), with 88% stereoselectivity and in 11% overall yield. Key steps are the following: (1) the asymmetric crotylborations of 8 and 12 that introduce the C(5), C(6), and C(8) stereocenters of 4; (2) the modified Suzuki coupling of vinylboronic acid 36 and dibromo olefin 31 that establishes the conjugated triene unit and introduces the C(9) Br steric directing group in a single operation; and (3) the highly stereoselective intramolecular Diels-Alder cycloaddition of tetraene 7. Stereochemical information obtained from the intramolecular Diels-Alder reactions of 25 and 26 provides a framework for rationalizing the role of the C(5) acetoxy group and the C(9) Br substituent on the stereoselectivity of the intramolecular Diels-Alder reaction of 7.

A HIGHLY STEREOSELECTIVE SYNTHESIS OF THE OCTAHYDRONAPHTHALENE SUBUNIT OF KIJANOLIDE AND TETRONOLIDE

A highly stereoselective synthesis of the octahydronaphtalene subunit 4 of kijanolide and tetronolide featuring the intramolecular Diels-Alder reaction of tetraenoate 5 is described.