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.
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.
Smith
Amos B
AB
Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Davulcu
Akin H
AH
Cho
Young Shin
YS
Ohmoto
Kazuyuki
K
Kürti
László
L
Ishiyama
Haruaki
H
D000447:Aldehydes / Q000737:chemistry; D000478:Alkylation; D000814:Aniline Compounds / Q000737:chemistry; D019905:Benzyl Alcohol / Q000737:chemistry; D001593:Benzyl Compounds / Q000737:chemistry; D004224:Diterpenes / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014052:Toluidines / Q000737:chemistry
D000447:Aldehydes; D000814:Aniline Compounds; D001593:Benzyl Compounds; D004224:Diterpenes; D004987:Ethers; D006835:Hydrazones; D007211:Indoles; D007783:Lactones; D014052:Toluidines; C030374:indole; D019905:Benzyl Alcohol; C023650:aniline; C038682:benzyl bromide