127995-73-7

Upstream product

• 13300-29-3 N⁶-methoxy-9-methyladenine 
• 126225-08-9 (5R,6S)-6-((3E,7E)-9-Bromo-3,7-dimethyl-nona-3,7-dienyl)-1,5,6-trimethyl-cyclohexene 
• 127891-14-9 (6R,7S)-6,7-Dimethyl-6-vinyl-1,4-dioxa-spiro[4.5]decane 
• 127717-10-6 (2RS,3SR)-2,3-dimethyl-2-ethenylcyclohexanone 
• 127717-12-8 6-(2-hydroxyethyl)-6,7-dimethyl-1,4-dioxaspiro<4.5>-decane 
• 127716-99-8 (2R,3S)-2,3-Dimethyl-2-vinyl-cyclohexanol 
• 127891-15-0 (6R,7S)-6-(2-Benzyloxy-ethyl)-6,7-dimethyl-1,4-dioxa-spiro[4.5]decane 
• 127891-27-4 (2E,6E)-3,7-Dimethyl-9-((1S,6R)-1,2,6-trimethyl-cyclohex-2-enyl)-nona-2,6-dien-1-ol 
• 127891-06-9 (2S,3R)-2-(2-Benzyloxy-ethyl)-2,3-dimethyl-cyclohexanone 
• 127891-09-2 ((2E,6E)-7-Bromo-3-methyl-octa-2,6-dienyloxymethyl)-benzene 
• 127891-16-1 (2R,3S)-2-(2-Benzyloxy-ethyl)-1,2,3-trimethyl-cyclohexanol 
• 127891-08-1 (2E,6E)-7-Bromo-3-methyl-octa-2,6-dienoic acid methyl ester 
• 127891-07-0 (5R,6S)-6-(2-Iodo-ethyl)-1,5,6-trimethyl-cyclohexene 
• 66408-80-8 (2E,6E)-2,6-dimethyl-8-((tetrahydro-2H-pyran-2-yl)oxy)octa-2,6-dien-1-ol 

Downstream Products

• 105026-04-8 Acetic acid 1-methyl-3-((1R,6S)-1,2,6-trimethyl-cyclohex-2-enyl)-propyl ester 
• 105026-08-2 4-((1R,6S)-1,2,6-Trimethyl-cyclohex-2-enyl)-butan-2-one 
• 105026-07-1 4-((1R,2S)-1,2-Dimethyl-6-methylene-cyclohexyl)-butan-2-one 
• 105026-06-0 4-((1R,6S)-1,2,6-Trimethyl-cyclohex-2-enyl)-butan-2-ol 
• 105026-03-7 Acetic acid 3-((1R,2S)-1,2-dimethyl-6-methylene-cyclohexyl)-1-methyl-propyl ester 
• 105026-02-6 Acetic acid 3-((1R,2R,6S)-2-hydroxy-1,2,6-trimethyl-cyclohexyl)-1-methyl-propyl ester 
• 105026-05-9 4-((1R,2S)-1,2-Dimethyl-6-methylene-cyclohexyl)-butan-2-ol 
• 105026-01-5 (1R,2R,3S)-2-(3-Hydroxy-butyl)-1,2,3-trimethyl-cyclohexanol 
• 88855-16-7 N-(4-Amino-6-methylamino-pyrimidin-5-yl)-N-[(2E,6E)-3,7-dimethyl-9-((1R,6S)-1,2,6-trimethyl-cyclohex-2-enyl)-nona-2,6-dienyl]-formamide 
• 626-95-9 1,4-Pentanediol 
• 92599-03-6 4-((1S,2R,3S,6R)-1,2,3-Trimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-butan-2-ol 

Relevant academic research and scientific papers

The First Synthesis of (–)-Agelasine F; an Antimycobacterial Natural Product Found in Marine Sponges in the Agelas Genus

(–)-Agelasine F (also known as ageline A) is a diterpene-adenine hybrid natural product isolated from marine sponges (Agelas species) and this compound is known to display cytotoxic activity against a variety of cancer cell lines as well as microorganisms. We herein report the first total synthesis of (–)-agelasine F. The commercially available and inexpensive monoterpenoid (S)-carvone was found to be a highly suitable starting material for the construction of the terpenoid part of the desired agelasine and controlling the stereochemistry of the target compound. Two alternative strategies from (S)-carvone were evaluated. Key-intermediates in the (–)-agelasine F synthesis are believed also to be valuable starting materials for total syntheses of other bioactive marine sponge metabolites. The synthetic route to (–)-agelasine F described herein is more efficient than previously published syntheses of racemic or ent-agelasine F.

TOTAL SYNTHESIS OF (+/-)-AGELINE A, A PHYSIOLOGICALLY ACTIVE CONSTITUENT OF AGELAS SPONGES

The monocyclic diterpene moiety of ageline A (1) was convergently constructed by the palladium-mediated coupling of C9-terpenic chain as vinyl bromide 10 and C11-monocyclic segment as alkylzinc compound 16, which was obtained through a stereoselective cyc