Frederick Ray Kinder

SYNTHETIC APPROACHES TOWARD THE BENGAMIDE FAMILY OF ANTITUMOR MARINE NATURAL PRODUCTS. A REVIEW

INTRODUCTION ..................................................................................................... ...................... ... 561 1 . Discovery .................................................................................................................................... 561 2 . Antitumor Activity Profile ........................................................................................................ 561 I . GENERAL ASPECTS ................................................................................................................ 563 1 . General Bengamide Retrosynthetic Analysis ......................................................................... 563 2 . Amide Coupling and Subsequent Reactions .......................................................................... 564 II . SYNTHESIS OF PROTECTED POLYHYDROxnATED BENGAMIDE SIDE-CHAIN INTERMEDIATES ............................................................................................ 566 1 . Synthesishm LGlucose ........................................................................................................ 566 2 . Synthesis from D-Glucose ....................................................................................................... 567 3 . Synthesis from LQuebrachitol ............................................................................................... 568 4 . Synthesis from (R)-Glyceraldehyde ........................................................................................ 569 5 . Synthesisfrom osD-Glucoheptonic I)clactone ........................................................................ 570 6 . Synthesis from D-Tarfaric Acid .............................................................................................. 572 III . SYNTHESES OF HYDROXYCYCLOLYSINE INTERMEDIAW ................................ 574 1 . Synthesis from (S)-Butunetriol ................................................................................................ 574 2 . Synthesisfrom LQuebrachitol ............................................................................................... 575 3 . Synthesis from LGlufamic Acid ............................................................................................. 576 4 . Synthesisfrom (SR)-S-Hydroxy-Llysine ................................................................................ 577 IV . SYNTHESES OF BENGAMIDE B ANALOGUES ............................................................... 578 REFERENCES ................................................................................................................................... 581