389091-80-9

Upstream product

• 944262-97-9 2-[5-((S)-Hydroxy-{(R)-4-[(E)-(S)-2-methoxymethyl-pyrrolidin-1-ylimino]-2,2,6,6-tetramethyl-tetrahydro-pyran-3-yl}-methyl)-4-iodo-2-methyl-phenyl]-isoindole-1,3-dione 
• 1197-66-6 2,2,6,6-tetramethyltetrahydropyran-4-one 
• 85-44-9 phthalic anhydride 
• 81863-45-8 3-(hydroxymethyl)-6-methylaniline 
• 389091-69-4 ((S)-2-Methoxymethyl-pyrrolidin-1-yl)-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-ylidene)-amine 
• 389091-74-1 5-(tert-butyl-dimethyl-silanyloxymethyl)-4-iodo-2-methyl-phenylamine 
• 389091-71-8 5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-iodo-4-methyl-benzaldehyde 
• 944262-94-6 2-(5-hydroxymethyl-4-iodo-2-methyl-phenyl)-isoindole-1,3-dione 
• 944263-04-1 2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-iodo-2-methyl-phenyl]-isoindole-1,3-dione 

Downstream Products

• 389091-67-2 Trifluoro-methanesulfonic acid (R)-3-{(S)-[5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-iodo-4-methyl-phenyl]-triethylsilanyloxy-methyl}-2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl ester 
• 389091-87-6 2-{4-Iodo-2-methyl-5-[(S)-((R)-2,2,6,6-tetramethyl-4-oxo-tetrahydro-pyran-3-yl)-triethylsilanyloxy-methyl]-phenyl}-isoindole-1,3-dione 

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.

Nodulisporic acid A synthetic studies. 1. Overall strategy and construction of a western hemisphere subtarget.

In this, the first of two Letters, we outline our overall strategy for the construction of (+)-nodulisporic acid A (1), a representative member of a new class of indole diterpenes. In addition, we describe the efficient assembly of (-)-6, an advanced western hemisphere subtarget, comprising the ABC rings of (+)-nodulisporic acid A (1). The synthesis proceeded in 9% overall yield (longest linear sequence, 11 steps), exploiting a Shibasaki-Mori tandem transmetalation-cyclization to construct ring B. [reaction: see text]