329362-97-2

Upstream product

• 67219-33-4 2-phenylmethanesulfonyl-benzothiazole 
• 133604-03-2 ethyl (4S)-5-(((tert-butyldiphenyl)silyl)oxy)-4-methyl-2(E)-pentenoate 
• 124887-13-4 (2S,3S,4R)-5-<(tert-butyl)diphenylsilyloxy>-2,4-dimethylpentane-1,3-diol 
• 127665-68-3 (4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol 
• 39760-56-0 triethyl 3-methyl-4-phosphonocrotonate 
• 329362-90-5 (2R,3R,4R,5S,E)-3,5-dimethoxy-2,4-dimethyl-7-phenylhept-6-enal 
• 1369677-40-6 C₂₅H₃₂O₄ 
• 1369677-38-2 C₂₃H₃₀O₃ 
• 1369677-36-0 C₂₃H₂₈O₃ 
• 176444-25-0 C₁₅H₂₂O₃ 
• 14371-10-9 (E)-3-phenylpropenal 
• 329362-91-6 (2R,3S,4E)-1-[4-benzyl-2-thioxo-(4S)-1,3-oxazolan-3-yl]-3-hydroxy-2-methyl-5-phenylpent-4-en-1-one 
• 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 

Downstream Products

• 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 

Relevant academic research and scientific papers

Step-economic synthesis of (+)-crocacin C: A concise crotylboronation/[3,3] -sigmatropic rearrangement approach

The step-economic total synthesis of (+)-crocacin C has been achieved in 20% yield from commercially available starting materials. This approach requires the isolation of only 8 intermediates and can provide a reliable supply of (+)-crocacin C for the development of new antifungal and crop protection agents.

Formal synthesis of (+)-crocacin C

The formal synthesis of (+)-crocacin C is reported. The approach described takes advantage of a highly regioselective epoxide cuprate addition and a diastereoselective Overman rearrangement. The synthesis is practical and amenable to scale up.

A formal total synthesis of crocacin C

An efficient total synthesis of a potent antifungal and moderate cytotoxic agent crocacin C is described. The synthesis involves the generation of four contiguous stereogenic centres via desymmetrization of a meso bicyclic dihydrofuran using asymmetric hy

Stereoselective formal synthesis of crocacin C via prins cyclization

A formal synthesis of crocacin C is described proving the versatility of Prins cyclization in natural product synthesis. The approach is convergent and highly stereoselective. Cross-metathesis and Heck reactions were utilized for the insertion of an aroma

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.