389091-69-4

Upstream product

• 1197-66-6 2,2,6,6-tetramethyltetrahydropyran-4-one 
• 59983-39-0 (S)-1-amino-2-(methoxymethyl)pyrrolidine 

Downstream Products

• 944262-95-7 2-(4-Iodo-5-{(S)-4-[(E)-(S)-2-methoxymethyl-pyrrolidin-1-ylimino]-2,2,6,6-tetramethyl-tetrahydro-pyran-3-ylmethyl}-2-methyl-phenyl)-isoindole-1,3-dione 
• 1197-66-6 2,2,6,6-tetramethyltetrahydropyran-4-one 
• 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 
• 389091-80-9 2-{5-[(S)-Hydroxy-((R)-2,2,6,6-tetramethyl-4-oxo-tetrahydro-pyran-3-yl)-methyl]-4-iodo-2-methyl-phenyl}-isoindole-1,3-dione 
• 887142-50-9 trifluoro-methanesulfonic acid 3-[5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-iodo-4-methyl-benzyl]-2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl ester 
• 887142-49-6 2-[4-Iodo-2-methyl-5-((R)-2,2,6,6-tetramethyl-4-oxo-tetrahydro-pyran-3-ylmethyl)-phenyl]-isoindole-1,3-dione 
• 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 
• 944263-05-2 2-[5-((R)-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 

Relevant academic research and scientific papers

An efficient protocol for the oxidative hydrolysis of ketone SAMP hydrazones employing SeO2 and H2O2 under buffered (pH 7) conditions

An effective oxidative protocol for the liberation of ketones from SAMP hydrazones employing peroxyselenous acid under aqueous buffered conditions (pH 7) has been developed. The procedure proceeds without epimerization of adjacent stereocenters or dehydration, in representative SAMP alkylation and aldol reaction adducts, respectively.

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]