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Journal ArticleDOI

Improved procedure for oxidations with the chromium trioxide-pyridine complex

01 Nov 1970-Journal of Organic Chemistry (American Chemical Society)-Vol. 35, Iss: 11, pp 4000-4002
About: This article is published in Journal of Organic Chemistry.The article was published on 1970-11-01. It has received 480 citations till now. The article focuses on the topics: Chromium trioxide & Pyridine.
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606 citations

Journal ArticleDOI
TL;DR: In this paper, a review of the stereocontrolled methods by which these fragments have been prepared for polyether sythesis and includes a survey of routes to spiroketals of other natural products.

602 citations

Journal ArticleDOI
TL;DR: The selected oleanane triterpenoid, CDDO, was found to be a potent, multifunctional agent in various in vitro assays and to show antiinflammatory activity against thioglycollate-interferon-gamma-induced mouse peritonitis.
Abstract: We have designed and synthesized 16 new olean- and urs-1-en-3-one triterpenoids with various modified rings C as potential antiinflammatory and cancer chemopreventive agents and evaluated their inhibitory activities against production of nitric oxide induced by interferon-γ in mouse macrophages. This investigation revealed that 9(11)-en-12-one and 12-en-11-one functionalities in ring C increase the potency by about 2−10 times compared with the original 12-ene. Subsequently, we have designed and synthesized novel olean- and urs-1-en-3-one derivatives with nitrile and carboxyl groups at C-2 in ring A and with 9(11)-en-12-one and 12-en-11-one functionalities in ring C. Among them, we have found that methyl 2-cyano-3, 12-dioxooleana-1,9(11)-dien-28-oate (25), 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO) (26), and methyl 2-carboxy-3,12-dioxooleana-1,9(11)-dien-28-oate (29) have extremely high potency (IC50 = 0.1 nM level). Their potency is similar to that of dexamethasone although they do not act t...

276 citations

Journal ArticleDOI

273 citations