887142-46-3

Upstream product

• 389103-79-1 (3aR,5aR,6R,7S,9aS,9bS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-6,9a,9b-trimethyl-decahydro-naphtho[1,2-c]furan-1-one 
• 100-39-0 benzyl bromide 
• 887138-29-6 (3aR,5aR,6R,7S,9aS,9bS)-7-Hydroxy-6-hydroxymethyl-6,9a,9b-trimethyl-decahydro-naphtho[1,2-c]furan-1-one 
• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 

Downstream Products

• 887142-53-2 2-((S)-7-Amino-1,1,3,3-tetramethyl-1,3,9,9a-tetrahydro-2-oxa-fluoren-6-yl)-1-((1S,2R,4aR,5R,6S,8aS)-5-benzyloxymethyl-2-hydroxymethyl-1,5,8a-trimethyl-6-triethylsilanyloxy-decahydro-naphthalen-1-yl)-ethanone 

Relevant academic research and scientific papers

Indole diterpene synthetic studies. Total synthesis of (+)-nodulisporic acid F and construction of the heptacyclic cores of (+)-nodulisporic acids A and B and (-)-nodulisporic acid D

(Chemical Equation Presented) A first-generation strategy for construction of (+)-nodulisporic acids A (1) and B (2) is described. The strategy entails union of the eastern and western hemisphere subtargets via the indole synthesis protocol developed in our laboratory. Subsequent elaboration of rings E and F, however, revealed the considerable acid instability of the C(24) hydroxyl, thereby preventing further advancement. Nonetheless, preparation of the heptacyclic core of (+)-nodulisporic acids A and B, the total synthesis of (+)-nodulisporic acid F, the simplest member of the nodulisporic acid family, and elaboration of the heptacyclic core of (-)-nodulisporic acid D were achieved.

Indole diterpenoid synthetic studies. Construction of the heptacyclic core of (-)-nodulisporic acid D

Construction of the heptacyclic core of (-)-nodulisporic acid D, a representative member of a recently discovered class of architecturally complex, ectoparasiticidal indole alkaloids, has been achieved. The modular synthetic strategy comprises an expedien