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.

研究了海洋聚醚大环内酯类化合物的全合成和立体化学归属的新方法。本课题以虾夷扇贝和甲藻中分离的贝类毒素pectenotoxin 2和甲藻中分离的抗真菌剂goniodomin A为目标化合物，对虾夷扇贝和甲藻中的两种贝类毒素进行了研究。计划在其全合成的最后阶段从其1-差向异构体衍生出果胶毒素2。以7-表果胶毒素2的C1-C7、C8-C20、C21-C30和C31-C40四个片段为原料，通过砜偶联、缩醛环化和烯烃复分解闭环反应，成功地合成了7-表果胶毒素2的全保护体。计划部分合成goniodomin A用于立体化学分配。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, S.-i.Souma, H.Mishima, A.Murai: "Total Synthesis of Prelaureatin."Synlett. 2002(9). 1493-1495 (2002)

K.Fujiwara、S.-i.Souma、H.Mishima、A.Murai：“Prelaureatin 的全合成”。Synlett。