887142-53-2

Upstream product

• 887142-46-3 (3aR,5aR,6R,7S,9aS,9bS)-6-Benzyloxymethyl-6,9a,9b-trimethyl-7-triethylsilanyloxy-decahydro-naphtho[1,2-c]furan-1-one 

Downstream Products

• 887142-44-1 [(1S,2R,4aR,5R,6S,8aS)-5-Benzyloxymethyl-1,5,8a-trimethyl-1-((S)-6,6,8,8-tetramethyl-6,8,8a,9-tetrahydro-1H-7-oxa-1-aza-cyclopenta[b]fluoren-2-yl)-6-triethylsilanyloxy-decahydro-naphthalen-2-yl]-methanol 

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