87360-02-9

Usage

InChI:InChI=1/C24H31NO3S/c1-16-13-17(2)15-18(14-16)25(29(27,28)19-9-7-6-8-10-19)21-20-11-12-24(5,22(21)26)23(20,3)4/h6-10,13-15,20-22,26H,11-12H2,1-5H3/t20-,21+,22+,24+/m1/s1

Upstream product

• 172374-00-4 (1R,2R,3S,4S)-<3--2-bornyl>-(1S,5R)-5-(5-tert-butyl-diphenyl-silyloxy-1-penten-2-yl)-2-oxo-cyclopentanecarboxylate 
• 67-56-1 methanol 
• 170117-11-0 (1R,2R,3S,4S)-<3--2-bornyl>-2-oxo-cyclohexenecarboxylate 
• 172490-96-9 (1R,2R,3S,4S)-<3--2-bornyl>-2-oxo-cyclopentene-carboxylate 
• 87360-00-7 (1R,4S)-3-[(E)-3,5-Dimethyl-phenylimino]-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 64-17-5 ethanol 
• 170117-08-5 (1R,2R,3S,4S)-<3--2-bornyl>-(6S)-2-hydroxy-6-phenyl-cyclohexenecarboxylate 
• 170117-07-4 (1R,2R,3S,4S)-<3--2-bornyl>-(6S)-2-hydroxy-6-isopropenyl-cyclohexenecarboxylate 
• 170211-90-2 (R)-6-Butyl-2-hydroxy-cyclohex-1-enecarboxylic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 170116-94-6 (S)-6-tert-Butyl-2-hydroxy-cyclohex-1-enecarboxylic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 170117-06-3 (1R,2R,3S,4S)-<3--2-bornyl>-(6S)-2-hydroxy-6-vinyl-cyclohexenecarboxylate 
• 170117-10-9 (R)-2-Hydroxy-6-methyl-cyclohex-1-enecarboxylic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 87360-01-8 (1R,3S,4S)-3-(3,5-Dimethyl-phenylamino)-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 172840-90-3 (1R,2R,3S,4S)-<3--2-bornyl>-(1R*)-2-oxo-1-phenylselenyl-cyclohexenecarboxylate 
• 172926-52-2 (1R,2R,3S,4S)-<3--2-bornyl>-(1S*)-2-oxo-1-phenylselenyl-cyclohexenecarboxylate 
• 172490-96-9 (1R,2R,3S,4S)-<3--2-bornyl>-2-oxo-cyclopentene-carboxylate 
• 172374-03-7 (1R,2R,3S,4S)-<3--2-bornyl>-(1S,5R)-5-tert-butyl-2-oxo-cyclopentanecarboxylate 
• 172505-34-9 (1R,2R,3S,4S)-<3--2-bornyl>-(1S,5R)-5-butyl-2-oxo-cyclopentanecarboxylate 
• 172840-93-6 (1R,2R,3S,4S)-<3--2-bornyl>-(1S,6R)-6-butyl-2-oxo-cyclohexanecarboxylate 
• 104282-54-4 (R)-3-p-Tolyl-butyric acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 102834-10-6 (Z)-But-2-enoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 104321-79-1 (E)-But-2-enoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 104321-81-5 (E)-4-Methyl-pent-2-enoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 104321-84-8 (S)-3-Methyl-pentanoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 104321-90-6 (R)-3-Methyl-pent-4-enoic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 

Relevant academic research and scientific papers

Asymmetric synthesis of a structurally simplified analogue of the antibiotic heptelidic acid

A structurally simplified analogue of the antibiotic (+)-heptelidic acid was synthesized in ten steps with an overall yield of 9%. Key step was a conjugate addition of a silyl protected vinylcuprate to an asymmetrically shielded enoate, which gave an addu

EPC Synthesis of (+)-Heptelidic Acid

An EPC (enantiomerically pure compound) synthesis of the antibiotic natural product (+)-heptelidic acid (1) is presented. Key step of the synthesis is a conjugate addition of the acetal protected vinyl cuprate 4 to the auxiliary shielded enoate 5n which g

A Short Synthesis of (-)-Chokol A

(-)-Chokol A (10) was prepared in six steps (22 percent overall yield) via conjugate addition of a higher order cyanocuprate to the chiral 2-oxo-cyclopentenecarboxylate 2n.After deprotection by transesterification the enantiomerically pure β-ketoester 5 was obtained which was transformed by α-methylation and subsequent decarbethoxylation to the cyclopentanone derivative 8.Addition of methylcerium dichloride resulted in a mixture of 9a, 9b and 9c (78:16:6), from which the main diastereomer 9a was separated by MPLC.Finally desilylation of 9a achieved (-)-chokol A (10).

EPC Synthesis of 6-Substituted 2-Oxo-cyclohexanecarboxylates via Conjugate Addition of Cuprates to Asymmetric Shielded 2-Oxo-cyclohexenecarboxylates

Asymmetric shielded 2-oxo-cyclohexenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclohexanecarboxylate 2 with camphor derived concave alcohols 1n and 1x and by subsequent introduction of a double bond via phenylselenides.Diastere

SYNTHESES OF DICTYOPTERENE B (HORMOSIRENE) AND ITS ENANTIOMER VIA ASYMMETRIC ScN' REACTIONS

Stereocontrolled syntheses of dictyopterene B (hormosirene) (1) and its enantiomer (ent-1) are reported.Key steps are highly stereoselective ScN' reactions of esters of alkohols 2 and 5 derived from (+)-camphor.

INFLUENCE OF CATION COMPLEXING SOLVENT ADDITIVES AND FUNCTIONAL GROUPS IN ASYMMETRIC ALKYLATIONS OF ESTERS VIA LITHIUM ENOLATES

Highly diastereoselective alkylations of propionates of chiral alcohols derived from (+)-camphor are described.It is demonstrated that steric shielding as well as cation complexation are important for stereoselection.The latter effects are in part rationa