124603-99-2

Upstream product

• 201230-82-2 carbon monoxide 
• 111692-59-2 (2R,2'S,3'aR,7'aR,4''S,5''R)-4''-<<4-(diphenylphosphino)benzoyl>oxy>-5''-methyl-3'a,6',7',7'a,3'',4'',5'',6''-octahydrodispiro-pyran> 
• 111675-18-4 C₃₃H₃₃O₆P 
• 97826-93-2 (3R,4S)-5<(tert-butyldimethylsilyl)oxy>3-hydroxy-1-<2(R)-<2(R)-<(4-methoxybenzyl)oxy>-3-cyclohexen-1(S)-yl>oxiranyl>-4-methyl-1-pentanone 
• 97905-63-0 (3S,4S)-5<(tert-butyldimethylsilyl)oxy>3-hydroxy-1-<2(R)-<2(R)-<(4-methoxybenzyl)oxy>-3-cyclohexen-1(S)-yl>oxiranyl>-4-methyl-1-pentanone 
• 124649-54-3 (3R,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-[(R)-2-((1S,2R)-2-hydroxy-cyclohex-3-enyl)-oxiranyl]-4-methyl-pentan-1-one 
• 124603-90-3 (3S,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-[(R)-2-((1S,2R)-2-hydroxy-cyclohex-3-enyl)-oxiranyl]-4-methyl-pentan-1-one 
• 124603-86-7 cis-2-<2-<(4-methoxybenzyl)oxy>-3-cyclohexen-1-yl>-2-propen-1-ol 1-acetate 
• 97905-62-9 2(S)-<2(R)-<(4-methoxybenzyl)oxy>-3-cyclohexen-1(S)-yl>oxiranemethanol 
• 124649-53-2 (2R,2'R,3'aR,7'aR,4''S,5''S)-4''-hydroxy-5''-methyl-3'a,6',7',7'a,3'',4'',5'',6''-octahydrodispiropyran> 
• 124649-55-4 (2R,2'S,3'aR,7'aR,4''R,5''S)-4''-hydroxy-5''-methyl-3'a,6',7',7'a,3'',4'',5'',6''-octahydrodispiropyran> 
• 97826-88-5 1-<2(R)-<2(R)-<(4-methoxybenzyl)oxy>-3-cyclohexen-1(S)-yl>oxiranyl>ethanone 
• 97826-92-1 2(R)-<2(R)-<(4-methoxybenzyl)oxy>-3-cyclohexen-1(S)-yl>oxiranecarbaldehyde 
• 124603-89-0 1-{(R)-2-[(1S,2R)-2-(4-Methoxy-benzyloxy)-cyclohex-3-enyl]-oxiranyl}-ethanol 

Downstream Products

• 111767-82-9 (2R,2'S,3'aR,7'S,7'aR,4''S,5''R)-4''-decahydro-4''-<<4-(diphenylphosphino)benzoyl>oxy>-5''-methyldispiro-pyran>-7'-carboxaldehyde 

Relevant academic research and scientific papers

Total Synthesis of (+)-Phyllanthocin. Introduction of Intramolecular Hydroformylation for Complex Molecule Functionalization

A 17-step total synthesis of (+)-phyllanthocin (1a) is described.Application of Sharpless'asymetric epoxidation reaction provided access to the diastereo- and enantiomerically pure epoxy ketone 9, a partner in crossed aldol construction.A notably rapid and high-yielding spiroketal equilibration leading to the tetracyclic intermediate 2 was effected with HF in acetonitrile.A Rh(I)-catalyzed hydroformylation was used to introduce the C3 functionality.Studies of intramolecular delivery of the rhodium nucleus to the concave face of the C3-C4 olefin led to a substantial improvement in yield and regioselectivity over the intermolecular version.

INTRAMOLECULAR PHOSPHINE-DIRECTED HYDROFORMYLATION. APPLICATION TO THE TOTAL SYNTHESIS OF (+)-PHYLLANTHOCIN

The temporary incorporation of a coordinating phosphine residue into the tetracyclic phyllanthocin precursor 1a directed the 2-catalyzed hydroformylation of 1d largely to the desired C(3) position .This "intramolecular hydroformylation" strategy substantially improves a key transformation in the total synthesis of (+)-phyllanthocin.