329362-91-6

Upstream product

• 145588-95-0 N-propanoyl-(S)-4-benzyl-1,3-oxazolidine-2-thione 
• 104-55-2 3-phenyl-propenal 
• 131744-19-9 (4S)-4-benzyl-1,3-oxazolidine-2-thione 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 329362-97-2 ethyl 7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-(2E,4E,6S,7S,8R,9S,10E)-2,4,10-undecatrienoate 
• 237425-38-6 7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-(2E,4E,6S,7S,8R,9S,10E)-2,4,10-undecatrienamide 
• 443123-81-7 (2E,4E,6S,7S,8R,9S,10E)-7,9-dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienoic acid 
• 922718-24-9 tert-Butyl-((E)-(2S,3S,4R,5S)-3,5-dimethoxy-2,4-dimethyl-7-phenyl-hept-6-enyloxy)-dimethyl-silane 
• 396718-49-3 1-tert-butyldimethylsilyloxy-4-methyl-7-phenyl-(2E,4S,5S,6E)-2,6-heptadiene-5-ol 
• 396718-50-6 1-tert-butyldimethylsilyloxy-5-methoxy-4-methyl-7-phenyl-(2E,4S,5S,6E)-2,6-heptadiene 
• 329362-96-1 5-methoxy-2,4-dimethyl-7-phenyl-(2S,3S,4S,5S,6E)-6-heptene-1,3-diol 
• 329362-92-7 ethyl 5-hydroxy-4-methyl-7-phenyl-(2E,4S,5S,6E)-2,6-heptadienoate 
• 307492-71-3 3,5-dimethoxy-2,4-dimethyl-7-phenyl-(2S,3S,4R,5S,6E)-6-hepten-1-ol 
• 329362-95-0 3-[2-methoxy-1-methyl-4-phenyl-(1R,2S,3E)-3-butenyl]-(2R,3R)-oxiran-2-yl methanol 
• 329362-90-5 (2R,3R,4R,5S,E)-3,5-dimethoxy-2,4-dimethyl-7-phenylhept-6-enal 
• 329362-94-9 5-methoxy-4-methyl-7-phenyl-(2E,4S,5S,6E)-2,6-heptadiene-1-ol 
• 329362-93-8 4-methyl-7-phenyl-(2E,4S,5S,6E)-2,6-heptadiene-1,5-diol 

Relevant academic research and scientific papers

Total synthesis of (+)-crocacin C

The total synthesis of potent antifungal and cytotoxic agent (+)-crocacin C in optically pure form following a convergent strategy is described here in detail. The synthesis also established the absolute stereochemistry of the molecule having a (6S,7S,8R,9S) configuration. While C8 and C9 stereocenters were built following a Ti(IV)-mediated diastereoselective 'non-Evans' aldol reaction based on 2-oxazolidinethione chiral auxiliary, lithium dimethylcuprate opening of a C6-C7 chiral epoxide prepared by Sharpless epoxidation method established the remaining two stereocentres.

Total synthesis of (+)-crocacin C

The first synthesis of (+)-crocacin C (3) in optically pure form is achieved following a convergent strategy. The synthesis also establishes the absolute stereochemistries of this novel class of potent antifungal and highly cytotoxic compounds. The naturally occurring crocacin C has (6S,7S,8R,9S) configuration, which is also the same for other congeners of the family, crocacins A, B and D.