Total Synthesis and Absolute Structure Determination of Marine Polyether Macrohdes.

海洋聚醚大分子的全合成和绝对结构测定。

• 批准号: 14580606
• 负责人: FUJIWARA Kenshu
• 金额: $ 2.3万
• 依托单位: Hokkaido University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2002
• 资助国家: 日本
• 起止时间: 2002 至 2003
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-14580606/
• 关键词: Marine Natural Products; Polyether Macrolide; Total Synthesis; Stereo-structure Determination; Pectenotoxins; Shellfish Poisoning; Cytotoxicity against Cancer Cells; Polyether Framework

New methodologies for total synthesis and stereochemical assignment of marine polyether macrolides were investigated. In this project, pectenotoxin 2,a diarrhetic shellfish toxin isolated from scallop Patinopecten yessoensis and dinoflagellate Dinophysis fortii, and goniodomin A, an antifungal agent isolated from dinoflagellate Alexandrium hiranoi (Goniodoma pseudogoniaulax), were selected as the synthetic targets. Pectenotoxin 2 was planned to be derived from its 1-epi congener at the final stage of its total synthesis. Full-protected form of the 7-epi-pectenotoxin 2 was successfully synthesized from four segments corresponding to the C1-C7,C8-C20,C21-C30 and C31-C40 parts, through a convergent process including sulfone-coupling, acetal-cyclization, and-ring-closing-olefin-metathesis reactions. Partial synthesis of goniodomin A was planned for the stereochemical assignment. Synthesis of the C1-C7,C6-C16,C15-C25, and C31-C36 fragments were established.

研究了海洋多醚大花环的全合成和立体化学分配的新方法。在这个项目中，pectenotoxin 2是一种从扇贝patinopecten Yessoensis和Dinoflagellate Dinophysis Fortii中分离出的腹泻抗毒素，而Goniodomin A则是一种从Dinofflagellate Alexandrium Hiranoi（Goniododomoma pseodogoxonyaia pseudogogogax）中分离出来的抗真菌剂A抗真菌剂。计划在其总合成的最后阶段源自其1-EPI同类物。 7-EPI-EDECENOTOXIN 2的全面保护形式是从与C1-C7，C8-C20，C21-C30和C31-C40零件相对应的四个片段成功合成的，该片段通过收敛过程，包括硫酮偶联，乙酰环基化，乙酰环状蛋白 - 固定 - 固定 - 固定 - 固定 - 固定 - 固定 - 固定 - 固定 - 裂解 - 裂解。计划为立体化学分配的促性腺毒素A的部分合成。建立了C1-C7，C6-C16，C15-C25和C31-C36片段的合成。

项目成果

K.Fujiwara, Y.Koyama, E.Doi, K.Shimawaki, Y.Ohtaniuchi, A.Takemura, S.-i.Souma, A.Murai: "Syntheses of the D-, E-, F-, and I-Ring Parts of Ciguatoxin by a Common Strategy Starting from Tri-O-acetyl-D-glucal."Synlett. 2002(9). 1496-1499 (2002)

K.Fujiwara、Y.Koyama、E.Doi、K.Shimawaki、Y.Ohtaniuchi、A.Takemura、S.-i.Souma、A.Murai：“D-、E-、F-和 I 的合成

Kenshu Fujiwara: "Synthesis of the D-,E-,F-, and I-Ring Part of Ciguatoxin by a Common Strategy Starting from Tri-O-acetyl-D-glucal"Synlett. No.9. 1496-1499 (2002)

Kenshu Fujiwara：“通过从三-O-乙酰基-D-葡萄糖开始的共同策略合成雪卡毒素的 D-、E-、F- 和 I-环部分”Synlett。

Kenshu Fujiwara: "Syntheses of the D-, E-, F-, and I-Ring Parts of Ciguatoxin by a Common Strategy Starting from Tri-O-acetyl-D-glucal"Synlett. No.9. 1496-1499 (2002)

Kenshu Fujiwara：“通过从三-O-乙酰基-D-葡萄糖开始的通用策略合成雪卡毒素的 D-、E-、F-和 I-环部分”Synlett。

Kenshu Fujiwara: "Total Synthesis of Prelaureatin."Synlett. No.9. 1493-1495 (2002)

Kenshu Fujiwara：“Prelaureatin 的全合成。”Synlett。

K.Fujiwara, Y.Koyama, K.Kawai, H.Tanaka, A.Murai: "Convergent Synthesis of the BCDE-Ring Part of Ciguatoxin"Synlett. 2002(11). 1835-1838 (2002)

K.Fujiwara、Y.Koyama、K.Kawai、H.Tanaka、A.Murai：“雪卡毒素 BCDE 环部分的收敛合成”Synlett。