99333-00-3

Upstream product

• 78508-96-0 (5S)-5-(hydroxymethyl)-5H-furan-2-one 
• 99315-75-0 (-)-5-O-(diphenyl-t-butylsilyl)-2,3-O-(thiocarbonyl)-D-ribono-1,4-lactone 
• 92512-33-9 (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 106795-88-4 (1R,6S,7S)-7-hydroxymethyl-8-oxabicyclo<4.3.0>non-3-en-9-one 
• 99315-76-1 (5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone 
• 106-99-0 buta-1,3-diene 

Downstream Products

• 99808-03-4 (1R,6S,7S)-7-diphenyl-t-butylsiloxymethyl-8-oxabicyclo-<4.3.0>non-3-ene 
• 99315-79-4 (+)-(1R,2S,5S)-2-diphenyl-t-butylsiloxymethyl-3-oxabicyclo<3.3.0>octan-7-one 
• 109917-94-4 [(2S,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-carboxymethyl-tetrahydro-furan-3-yl]-acetic acid 
• 99315-78-3 (2S,3R,4S)-2-diphenyl-t-butylsiloxymethyl-3,4-bis(methoxycarbonylmethyl)tetrahydrofuran 

Relevant academic research and scientific papers

Synthesis and Evaluation of a 2,11-Cembranoid-Inspired Library

The 2,11-cembranoid family of natural products has been used as inspiration for the synthesis of a structurally simplified, functionally diverse library of octahydroisobenzofuran-based compounds designed to augment a typical medicinal chemistry library screen. Ring-closing metathesis, lactonisation and SmI2-mediated methods were exemplified and applied to the installation of a third ring to mimic the nine-membered ring of the 2,11-cembranoids. The library was assessed for aqueous solubility and permeability, with a chemical-space analysis performed for comparison to the family of cembranoid natural products and a sample set of a screening library. Preliminary investigations in cancer cells showed that the simpler scaffolds could recapitulate the reported anti-migratory activity of the natural products. Building a bridge: A library of compounds based on the naturally occurring 2,11-cembranoid family has been synthesised by using different synthetic strategies. The library was found to cover the space between the natural products and a screening library sample set (see figure). The new compounds were shown to recapitulate reported activities of the natural products.

Synthesis and anti-HIV activity of conformationally restricted bicyclic hexahydroisobenzofuran nucleoside analogs

A chiral synthesis of a series of hexahydroisobenzofuran (HIBF) nucleosides has been accomplished via glycosylation of a stereo-defined (syn-isomer) sugar motif 16 with the appropriate silylated bases. All nucleoside analogs were obtained in 52-71% yield as a mixture of α- and β-anomeric products increasing the breadth of the novel nucleosides available for screening. The structure of the novel bicyclic HIBF nucleosides was established by a single crystal X-ray structure of the β-HIBF thymine analog 22b. Furthermore, the sugar conformation for these nucleosides was established as N-type. Among the novel HIBF nucleosides synthesized, twenty-five compounds were tested as inhibitor of HIV-1 in human peripheral blood mononuclear (PBM) cells and seven were found to be active (EC50 = 12.3-36.2 μM). Six of these compounds were purine analogs with β-HIBF inosine analog 22o being the most potent (EC50 = 12.3 μM) among all compounds tested. The striking resemblance between didanosine (ddI) and 22o may explain the potent anti-HIV activity.

Cycloaddition and one-carbon homologation studies in the synthesis of advanced iridoid precursors

A Diels-Alder cycloaddition approach to the sweroside aglycone intermediate of iridoids was explored using silylated butenolides and levoglucosenone as dienophiles under both Lewis acid and thermal conditions. Results of this study reveal no evidence that

Norrisolide: Total synthesis and related studies

A stereoselective synthesis of (+)-norrisolide is presented. This natural product belongs to a family of marine spongiane diterpenes the structure of which is characterized by a fused γ-lactone-γ-lactol ring system attached to a bicyclic hydrophobic core.

Stereoselective Total Synthesis of (+)-Norrisolide

In a convergent approach to the marine natural product (+)-norrisolide (1) the two bicyclic ring systems are coupled through the C9-C10 bond to assemble the carbon framework in a late stage of the synthesis. Other highlights of the synthetic strategy incl

DIELS-ALDER CYCLOADDITIONS OF CHIRAL BUTENOLIDES WITH BUTADIENE AND ISOPRENE: DIASTEREOFACIAL SELECTIVITY AND REGIOSELECTIVITY

Chiral butenolides react with butandiene at 210 deg C giving optically active bicyclic compounds wiht excellent diastereoselectivity, in good yields.Optical purity of the adducts has been verified either by chemical correlation and/or by the use of Eu(hfc

Chiral Oxabicyclic Systems from Ribonolactone

We describe the synthesis of (-)-5-O-diphenyl-t-butylsiloxymethyl-5H-furan-2-one (4) from D-ribonolactone; conversion of this chiral butenolide into (+)-(1R,6S,7S)-7-diphenyl-t-butylsiloxymethyl-8-oxabicyclonon-3-en-9-one (10) (by means of a Diels-

Chiral Bicycles from Ribonolactone

The preparation of the chiral butenolide (4b) is described, together with its use in annulation reactions yielding stereochemically defined bicyclo, , and ring systems; the synthetic utility of these species is indicated.