Alpha-amination of labdane-type diterpenes by organocatalysis

نویسندگان

چکیده

The first electrophilic α-amination reaction of labdane-type diterpene (−)-(5S,9S,10S,13S)-labd-7-en-15-oic acid and (+)-(5S,8R,9R,10S,13R)-8-hydroxylabdan-15-oic acid, isolated from aerial parts Ageratina jocotepecana is presented. In the presence dibenzylazodicarboxylate proline followed by an in situ reduction, corresponding hydrazino alcohols were obtained. It demonstrated that moiety had no influence diastereoselectivity then controlled catalyst used, at opposite to second mainly control diastereochemistry product.

برای دانلود باید عضویت طلایی داشته باشید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Five new labdane diterpenes from Aster oharai.

Five new labdane diterpenes (1-5) together with seven known diterpenes have been isolated from a methanol extract of the aerial parts of Aster oharai. Five new structures were determined as 7alpha-hydroperoxylabda-8(17),14-dien-13(R)-ol-4-O-acetyl-alpha-L-6-deoxyidopyranoside (1), 7alpha-hydroperoxylabda-8,14-dien-13(R)-ol-4-O-acetyl-alpha-L-6-deoxyidopyranoside (2), labda-7,14-dien-13(R)-ol-4-...

متن کامل

Dimeric labdane diterpenes: synthesis and antiproliferative effects.

Several diterpenes with the labdane skeleton show biological activity, including antiproliferative effects. Most of the research work on bioactive labdanes has been carried out on naturally occurring diterpenes and semisynthetic derivatives, but much less is known on the effects of diterpene dimers. The aim of the present work was to synthesize dimeric diterpenes from the labdane imbricatolic a...

متن کامل

Labdane Diterpenes from the Fruits of Sinopodophyllum emodi.

Two new labdane diterpenes, sinoditerpene A (1) and B (2), were isolated from the fruits of Sinopodophyllum emodi, along with two known analogues 3 and 4. Their structures were established on the basis of extensive spectroscopic analysis. The isolation of compounds 1-4 represents the first report of diterpenes from the genus Sinopodophyllum. The cytotoxic activities of all isolated compounds we...

متن کامل

New Cytotoxic Seco-Type Triterpene and Labdane-Type Diterpenes from Nuxia oppositifolia.

Chromatographic purification of the n-hexane and dichloromethane extracts of Nuxia oppositifolia aerial parts, growing in Saudi Arabia, resulted in the isolation and characterization of three new labdane-type diterpene acids, 2β-acetoxy-labda-7-en-15-oic acid (1), 2β-acetoxy-7-oxolabda-8-en-15-oic acid (2), 2β-acetoxy-6-oxolabda-7-en-15-oic acid (3), and one new seco-triterpene, 3,4-seco olean-...

متن کامل

A modular approach for facile biosynthesis of labdane-related diterpenes.

Labdane-related diterpenoids are a large group of over 5,000 natural products whose biosynthesis typically proceeds through a labdadienyl/copalyl diphosphate (CPP) intermediate to a further cyclized and/or rearranged hydrocarbon diterpene en route to more elaborated compounds. Here we report a modular approach for facile biosynthesis of labdane-related diterpenes wherein base pGGxC vectors capa...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

ژورنال

عنوان ژورنال: Synthetic Communications

سال: 2022

ISSN: ['1532-2432', '0039-7911']

DOI: https://doi.org/10.1080/00397911.2022.2032174