109262-86-4Relevant academic research and scientific papers
Synthesis and structure-activity relationship study of FD-891: Importance of the side chain and C8-C9 epoxide for cytotoxic activity against cancer cells
Itagaki, Tomohiro,Kawamata, Ayano,Takeuchi, Miho,Hamada, Keisuke,Iwabuchi, Yoshiharu,Eguchi, Tadashi,Kudo, Fumitaka,Usui, Takeo,Kanoh, Naoki
, p. 287 - 293 (2016/05/09)
Unified synthesis of FD-891 analogs and their structure-activity relationship are described. By using stereoselective allylation/crotylation and Evans aldol chemistry, six side-chain fragments having different length and terminus were synthesized. These f
Total Synthesis, Stereochemical Revision, and Biological Reassessment of MandelalideA: Chemical Mimicry of Intrafamily Relationships
Willwacher, Jens,Heggen, Berit,Wirtz, Conny,Thiel, Walter,Fürstner, Alois
supporting information, p. 10416 - 10430 (2015/07/07)
MandelalideA and three congeners had recently been isolated as the supposedly highly cytotoxic principles of an ascidian collected off the South African coastline. Since these compounds are hardly available from the natural source, a concise synthesis rou
Practical, highly stereoselective allyl- and crotylsilylation of aldehydes catalyzed by readily available Cinchona alkaloid amide
Huang, Yuan,Yang, Licheng,Shao, Panlin,Zhao, Yu
, p. 3275 - 3281 (2013/07/26)
We have demonstrated that bidentate Lewis base catalysts can be constructed based on the Cinchona alkaloid structure that promote highly stereoselective reactions of allyl- and crotyltrichlorosilane with aromatic as well as aliphatic aldehydes (90-99% ee, >98% diastereoselectivity). The catalysts are available in a one-pot procedure in >70% yield from cheap starting materials and promote the allylation reactions at ambient temperature. Gram scale reactions with catalyst recovery and reuse showcased the practicality of the catalytic system.
Synthesis of the ABC ring fragment of brevisin, a new dinoflagellate polycyclic ether
Ohtani, Naohito,Tsutsumi, Ryosuke,Kuranaga, Takefumi,Shirai, Tomohiro,Wright, Jeffrey L.C.,Baden, Daniel G.,Satake, Masayuki,Tachibana, Kazuo
scheme or table, p. 825 - 830 (2010/10/03)
A polycyclic ether, brevisin was isolated from the red-tide dinoflagellate Karenia brevis. Its unique skeletal structure consists of two separate tricyclic ether assemblies connected by a methylene bridge. The ABC ring fragment of brevisin was synthesized
Total synthesis of (+)-calyculin A and (-)-calyculin B: Asymmetric synthesis of the C(9-25) spiroketal dipropionate subunit
Smith III, Amos B.,Friestad, Gregory K.,Barbosa, Joseph,Bertounesque, Emmanuel,Hull, Kenneth G.,Iwashima, Makoto,Qiu, Yuping,Salvatore, Brian A.,Spoors, P. Grant,Duan, James J.-W
, p. 10468 - 10477 (2007/10/03)
An asymmetric synthesis of the stereochemically fully endowed C(9-25) spiroketal fragment (+)-BC of the calyculins (1-8) is described. Highlights of the synthesis include: a highly diastereoselective IBr-induced iodocarbonate cyclization to introduce the
CALYCULIN SYNTHETIC STUDIES. STEREOSELECTIVE CONSTRUCTION OF THE C(14)-C(25) SPIROKETAL SUBUNIT
Smith, Amos B.,Duan, James J.-W.,Hull, Kenneth G.,Salvatore, Brian A.
, p. 4855 - 4858 (2007/10/02)
A convergent, stereocontrolled synthesis of the spiroketal fragment of calyculins A-H has been achieved.Key transformations include the novel iodine monobromide-induced iodocarbonate cyclization of (+)-19, efficient coupling of epoxide (+)-14 with the ste
BASE-ASSISTED MIGRATION OF TRIMETHYLSILYL GROUP FROM CARBON TO OXYGEN IN γ-TRIMETHYLSILYL-γ,δ-UNSATURATED ALCOHOLS, γ-TRIMETHYLSILYL-γ,δ-EPOXY ALCOHOLS, AND β-TRIMETHYLSILYL-β,γ-EPOXY ALCOHOLS TO THE CORRESPONDING SILYL ETHERS
Kobayashi, Yuichi,Uchiyama, Hiroshi,Kanbara, Hiroshi,Kusakabe, Masato,Sato, Fumie
, p. 549 - 561 (2007/10/02)
Treatment of γ-trimethylsilyl-γ,δ-unsaturated alcohols 2, γ-trimethylsilyl-γ,δ-epoxy alcohols 3-6, and β-trimethylsilyl-β,γ-epoxy alcohols 9-12 with NaH in HMPA or t-BuOK in THF brought about facile migration of SiMe3 group from carbon to oxygen to produc
