Abstract
The first total syntheses of salmoxanthin and deepoxysalmoxanthin were accomplished by stereoselective Wittig reaction of a C15-tri-n-butylphosphonium salt bearing a 3,6-dihydroxy-ε-end group with the corresponding C25- apocarotenals. The 3,6-dihydroxy-ε-end moiety was constructed by chemo- and stereoselective reduction of the γ- hydroxy-α,β-cyclohexenone derivative.
Keywords: Carotenoids, chemo- and stereoselective reduction, deepoxysalmoxanthin, salmoxanthin, stereoselective Wittig reaction, total synthesis.
Current Organic Synthesis
Title:Stereocontrolled First Total Syntheses of Salmoxanthin and Deepoxysalmoxanthin
Volume: 12 Issue: 2
Author(s): Yumiko Yamano, Katsuhiro Eno, Yukari Hikita, Hiromasa Kurimoto and Akimori Wada
Affiliation:
Keywords: Carotenoids, chemo- and stereoselective reduction, deepoxysalmoxanthin, salmoxanthin, stereoselective Wittig reaction, total synthesis.
Abstract: The first total syntheses of salmoxanthin and deepoxysalmoxanthin were accomplished by stereoselective Wittig reaction of a C15-tri-n-butylphosphonium salt bearing a 3,6-dihydroxy-ε-end group with the corresponding C25- apocarotenals. The 3,6-dihydroxy-ε-end moiety was constructed by chemo- and stereoselective reduction of the γ- hydroxy-α,β-cyclohexenone derivative.
Export Options
About this article
Cite this article as:
Yamano Yumiko, Eno Katsuhiro, Hikita Yukari, Kurimoto Hiromasa and Wada Akimori, Stereocontrolled First Total Syntheses of Salmoxanthin and Deepoxysalmoxanthin, Current Organic Synthesis 2015; 12 (2) . https://dx.doi.org/10.2174/1570179411999141106102507
DOI https://dx.doi.org/10.2174/1570179411999141106102507 |
Print ISSN 1570-1794 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6271 |
Call for Papers in Thematic Issues
Biorthogonal Chemistry: A translational chemical tool for in vivo applications
After the discovery in 1990, bioorthogonal chemistry encompassed a set of diverse fast-paced selective chemical reactions, facilitating the study of biomolecules under physiological aura without intervening in the biochemical processes. Over the past two decades, significant progress has been witnessed in bioorthogonal reactions such as Staudinger ligation, metal-catalyzed coupling reactions, ...read more
Design and Synthesis of Green Pesticides
The development of green new pesticides is currently one of the hotspots in the field of pesticide research, aiming to develop efficient, environmentally friendly, and safe pesticide products to meet the needs of modern agricultural production. Green new pesticides prioritize environmental friendliness and ecological safety. Therefore, during the research and ...read more
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
Organic Radical Chemistry
Organic radical chemistry has a history of more than 110 years. In the past decade, we have witnessed new directions for organic radical chemistry. It has now become an exciting area of research in organic chemistry, and new discoveries can be seen every day in various aspects of radical chemistry ...read more
Related Journals
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers