𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Stereoselective synthesis of [11 β-3H]prostaglandin E1

✍ Scribed by G. L. Bundy; J. A. Easter; L. S. Banitt; Y. Philopoulos; A. J. Wickrema Sinha; R. S. P. Hsi

Publisher
John Wiley and Sons
Year
1993
Tongue
French
Weight
533 KB
Volume
33
Category
Article
ISSN
0022-2135

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

This report describes an efficient stereoselective synthesis of [11β‐^3^H]prostaglandin E~1~ ([11β‐^3^H]PGE~1~). The key multiply protected 11‐keto intermediate was prepared in only three steps from PGE~1~. Reduction of the ketone function at C‐11 with sodium borodeuteride and sodium borotritide, followed by sequential removal of protecting groups, afforded PGE~1~ labeled with deuterium and tritium, respectively, at the 11‐beta position. The reduction and deprotection were accomplished in one reaction flask without requiring purification of intermediates. Trace amounts of C~11~‐epimer formed in the reduction were readily separated by means of preparative reversed‐phase HPLC. Using sodium borotritide of nominally 67 Ci/mmol, we obtained [11β‐^3^H]PGE~1~ with specific activity of 15 Ci/mmol. A disposition study in the monkey with intravenous administration of this material indicated excellent in vivo metabolic stability of the 11β‐tritium label.

📜 SIMILAR VOLUMES

Stereoselective Total Synthesis of (11β)
Stereoselective Total Synthesis of (11β)-11-Methoxycurvularin
✍ Karuturi Rajesh; Vangaru Suresh; Jondoss Jon Paul Selvam; Dokuburra Chanti Babu; 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 German ⚖ 164 KB

## Abstract A simple and highly efficient stereoselective total synthesis of (11__β__)‐11‐methoxycurvularin (**5**), a polyketide natural product, was achieved. The synthesis commenced with a Cu‐mediated regioselective opening of (2__S__)‐2‐methyloxirane (**6**) and comprised a __Keck__ asymmetric

Synthesis Of [11β-3H]prostacyclin
Synthesis Of [11β-3H]prostacyclin
✍ Ian A. Blair; Christopher N. Hensby; John Macdermot 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 French ⚖ 292 KB

## Abstract The synthesis of [11β‐^3^H]prostacyclin and [11β‐^3^H]6‐oxo‐prostaglandin F~1α~ has been described. The strategy involved borotritide reduction of prostaglandin D~2~, followed by cyclic iodoether formation. Adenylate cyclase activation in a neuronal somatic cell hybrid and GC‐MS were us

Stereoselective Synthesis of 8-Aza-9,11-
Stereoselective Synthesis of 8-Aza-9,11-ethenoprostaglandin H1
✍ Barco, Achille ;Benetti, Simonetta ;Baraldi, Pier Giovanni ;Moroder, Fabio ;Poll 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 English ⚖ 309 KB

## Abstract A stereoselective synthesis of the title compound [8‐aza‐9,11‐etheno‐PGH~1~ (3)] starting from butyl 2‐(__p__‐tolylsulfonyl)‐2‐azabicyclo[2.2.1]hept‐5‐ene‐__exo__‐3‐carboxylate (**5**) is described.

Synthesis of tracer labelled [11,12-3H]-
Synthesis of tracer labelled [11,12-3H]-β-carotene
✍ Bhabesh C. Goswami; Arun B. Barua 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 French ⚖ 94 KB

## Abstract The synthesis of tracer labelled [11,12‐^3^H]‐β‐carotene is described. The procedure uses Wittig condensation of tracer labelled ^3^H‐retinal (retinal spiked with [11,12‐^3^H]‐retinal) with retinyl triphenylphosphonium bromide. The preparation of tracer labelled[^3^H]‐β‐carotene is suit

Preparation of [3H]-labelled prostagland
Preparation of [3H]-labelled prostaglandin E1 by hydrogenation of prostaglandin E2 over RhCl(PPH3)3. An example of selectivity in homogeneous hydrogenation
✍ G. K. Koch; J. W. Dalenberg 📂 Article 📅 1970 🏛 John Wiley and Sons 🌐 French ⚖ 169 KB

Labelled prostaglandin El (PGE,) (Fig. l), which is used in biochemical and biological studies, can be prepared biosynthetically from labelled dihomo-y-linolenic acid or, particularly when high specific activities are required, by catalytic hydrogenation of prostaglandin E, (PGE,) over a Pd-C-cataly