142633-11-2Relevant academic research and scientific papers
Total synthesis of the light-harvesting carotenoid peridinin
Olpp, Thomas,Brueckner, Reinhard
, p. 4023 - 4027 (2006)
(Chemical Equation Presented) Light work: The light-harvesting marine C37 carotenoid peridinin was synthesized from (+)-diethyl tartrate and (-)-actinol. Key transformations were the differential reduction of an ester-containing Weinreb amide,
Stereoretentive suzuki-miyaura coupling of haloallenes enables fully stereocontrolled access to (-)-Peridinin
Woerly, Eric M.,Cherney, Alan H.,Davis, Erin K.,Burke, Martin D.
supporting information; experimental part, p. 6941 - 6943 (2010/08/06)
Stimulated by the substantial challenge of synthesizing the complex and sensitive stereogenic allene-containing core of (-)-peridinin, the first stereocontrolled coupling of haloallenes with boronic acids has been achieved. This new method and the principles that emerged during its development stand to enable the more efficient and flexible preparation of a wide range of natural products, pharmaceuticals, and intermediates that possess a stereogenic allene motif. This new reaction was harnessed to achieve the first completely stereocontrolled total synthesis of (-)-peridinin. This synthesis was accomplished using only one reaction iteratively to assemble four fully functionalized building blocks with complete stereoretention at each initial halide or boron-bearing carbon. This synthesis elevates the capacity of the iterative cross-coupling strategy to an unprecedented benchmark. Moreover, the efficient and highly modular nature of this synthesis promises to enable systematic dissection of the heretofore enigmatic structure/function relationships that underlie the protein-like antilipoperoxidant activities of this remarkable small molecule natural product.
Total synthesis of peridinin and related C37-norcarotenoid butenolides
Vaz, Belen,Dominguez, Marta,Alvarez, Rosana,De Lera, Angel R.
, p. 1273 - 1290 (2007/10/03)
As an extension of our synthesis of symmetrical carotenoids, the preparation of the highly functionalized C37-norcarotenoid butenolide peridinin (1), its 6′-epi- and 11′Z stereoisomers has been completed. Featuring a central dihalogenated Csub
The stille reaction in the synthesis of carotenoid butenolides: Synthesis of S′-epi-pridinin
Vaz, Belen,Alvarez, Rosana,Brueckner, Reinhard,De Lera, Angel R.
, p. 545 - 548 (2007/10/03)
(Chemical Equation Presented) A new strategy for carotenoid butenolides has been developed that is based in part in halogen-selective Stille cross-coupling of dihalogenated ylidenebutenolide segment 2 and highly functionalized alkenylstannanes.
Stereocontrolled total synthesis of a polyfunctional carotenoid, peridinin
Furuichi, Noriyuki,Hara, Hirokazu,Osaki, Takashi,Nakano, Masayuki,Mori, Hajime,Katsumura, Shigeo
, p. 7949 - 7959 (2007/10/03)
Peridinin, which was isolated from the planktonic algae dinoflagellates causing red tides, is a highly oxidized carotenoid containing an allene and a characteristic (Z)-γ-ylidenebutenolide function in the main conjugated polyene chain in addition to funct
A novel photoproduct of peridinin, A 6S allenic isomer
Yamano, Yumiko,Sumiya, Sanae,Suzuki, Keiko,Kurimoto, Yoshitaka,Koyama, Yasushi,Shimamura, Toshio,Ito, Masayoshi
, p. 2991 - 2994 (2007/10/02)
Iodine catalyzed photoisomerization of peridinin gave the novel 6S allenic isomer whose structure was proved by chemical synthesis.
