𝔖 Bobbio Scriptorium
✦   LIBER   ✦

C45- and C50-Carotehoids. Part 8. Synthesis of (all-E,2S,2′S)-bacterioruberin, (all-E,2S,2′S)-monoanhydrobacterioruberin, (all-E,2S,2′S)-bisanhydrobacterioruberin, (all- E,2R,2′R)-3,4,3′,4′-tetrahydrobisanhydro- bacterioruberin, and (all-E,S)-2-isopentenyl-3,4-dehydrorhodopin

✍ Scribed by Ivo Lakomy; Daniel Sarbach; Bruno Traber; Christoph Arm; Daniel Zuber; Hanspeter Pfander; Klaus Noack

Publisher
John Wiley and Sons
Year
1997
Tongue
German
Weight
786 KB
Volume
80
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Starting from (R)‐3‐hydroxybutyric acid ((R)‐10) the C~45~‐ and C~50~‐carotenoids (all‐E,2__S__,2′S)‐bacterioruberm (1), (all‐E,2__S__,2′S)‐monoanhydrobacterioruberin (2), (all‐E,2__S__,2′S)‐bisanhydrobacterioruberin (3), (all‐E,2__R__,2′R)‐3,4,3′,4′‐tetrahydrobisanhydrobacterioruberin (5), and (all‐E,S)‐2‐isopentenyl‐3,4‐dehydrorhodopin (6) were synthesized. By comparison of the chiroptical data of the natural and the synthetic compounds, the (2__S__)‐ and (2′S)‐configuration of the natural products 1–3 and 6 was established.

📜 SIMILAR VOLUMES

ChemInform Abstract: C45- and C50-Carote
ChemInform Abstract: C45- and C50-Carotenoids. Part 8. Synthesis of (all-E,2S,2′S)- Bacterioruberin, (all-E,2S,2′S)-Monoanhydrobacterioruberin, (all-E,2S, 2′S)-Bisanhydrobacterioruberin, (all-E,2R,2′R)-3,4,3′,4′- Tetrahydrobisanhydrobacterioruberin, and (all-E,S)-2-Isopentenyl-3,4- dehydrorhodopin.
✍ I. LAKOMY; D. SARBACH; B. TRABER; C. ARM; D. ZUBER; H. PFANDER; K. NOACK 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 29 KB 👁 1 views
C45- and C50-Carotenoids Part7 Total syn
C45- and C50-Carotenoids Part7 Total synthesis of (all-E,2R,6R,2′R,6′R)- and (all-E,2R,6S,2′R,6′S)-2,2′-Bis(4-hydroxy-3-methylbut-2-enyl)-γ,γ-carotene (sarcinaxanthin)
✍ Marc Lanz; Birgit Bartels; Hanspeter Pfander 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 German ⚖ 929 KB

## Abstract The synthesis of sarcinaxanthin ((__2R,6R,2′R,6′R__)‐1), a symmetrical C~50~‐carotenoid with two γ‐end groups, isolated from __Sarcina lutea__ and from __Cellulomonas biazotea__ as major pigment, was based on the strategy C~20~ + C~10~ + C~20~ = C~50~ using camphoric acid as starting ma

Synthesis of 13C-labelled (all-E,3R,3′R)
Synthesis of 13C-labelled (all-E,3R,3′R)-β,β-carotene-3,3′-diol (zeaxanthin) at C(12), C(13), C(12′), and C(13′) via all-E-2,7-dimethylocta-2,4,6-triene-1,8-dial-13C4
✍ Frederick Khachik; Gary R. Beecher; Betty W. Li; Gerhard Englert 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 French ⚖ 668 KB

## Abstract The title compound (10) has been synthesized from all‐E‐2,7‐ dimethylocta‐2,4,6‐triene‐1,8‐dial (C~10~‐dialdehyde, 8) labelled with four ^13^C from commercially available and relatively inexpensive starting materials. The key starting material in this synthesis, (EtO)~2~P(O)^13^CHMe^13^

Stéréochimie de (2S, 4S, 5R;2S, 4S, 5S)-
Stéréochimie de (2S, 4S, 5R;2S, 4S, 5S)- et (2R, 4S, 5R;2R, 4S, 5S)-2-alkyl-1,3,4-triméthyl-5-phénylimidazolidines déterminée par RMN-−1H et -−13C
✍ D. Tytgat; M. Gelbcke 📂 Article 📅 2010 🏛 Wiley (John Wiley & Sons) ⚖ 339 KB 👁 1 views

The condensation of (1 R,2S) or (lS,2S)-N,N'-dimethyI-l-phenylpropane-l 2-diamines with aldehydes gives respectively two diastereorneric 2-alkyl-l,3,4-trimethyI-S-phen limidazolidines. At thermodynamical equilibrium the major isomer in the erythro series is this one where t f ! e substituents at pos

Deuterated anabolic drugs. Part 2 synthe
Deuterated anabolic drugs. Part 2 synthesis of (R,S)-3, 4-bis(4-hydroxyphenyl)-[2,2,5,5-d 4]hexane (HEX-d4) and (E,E)-3,4-bis(4-hydroxyphenyl)-[2,5-d2]hexa-2,4-diene (DE-d2)
✍ Gijsbert Zomer; Henk J. G. M. Derks; Hans Wynberg 📂 Article 📅 1984 🏛 John Wiley and Sons 🌐 French ⚖ 223 KB 👁 1 views

D e u t e r a t e d a n a b o l i c d r u g s . P a r t 2 S y n t h e s i s o f ( R , S ) -3 , 4 -b i s ( 4-hydroxyphenyl)-[2,2,5,5-d l h e x a n e ( HEX-d a n d (E,E)-3,4-bis(4-hydroxyphenyl)-[2,5-d l h e x a -2 , 4 -d i e n e (DE-d ) 4 4 2 2 G i j s b e r t Zomer, Henk J.C.M. D e r k s a n d H a n