Abstract
Covering: up to 2017This review highlights why careful consideration of the biosynthetic origin (the how) and the biological function (the why) of a natural product can be so useful during the determination of its structure. Recent examples of structural reassignments inspired by biosynthetic and functional insights will be presented. This review will demonstrate the importance of viewing the origin, structure and function of a natural product as intertwined threads of a single story, best viewed as a whole rather than as discrete topics.
Highlights
IntroductionWhen faced with a natural product it is prudent to carefully consider how and why it exists
2 Case studies 2.1 Cytosporolides A–C 2.2 Incargranine B 2.3 Caraphenols B and C 2.4 Yuremamine 2.5 Streptorubin B/butylcycloheptylprodigiosin 2.6 Tridachiahydropyrones 3 Conclusions 4 Con icts of interest 5 Acknowledgements 6 References
The serendipitous reassignment of natural products during biomimetic syntheses is showcased in Calvert and Sperry's total synthesis of yuremamine (Section 2.4)
Summary
When faced with a natural product it is prudent to carefully consider how and why it exists. This will typically include some, or all, of the following steps:. (4) Consideration of any known or proposed functional roles If nothing else, these relatively straightforward steps can serve as a reassuring check that any proposed structure, if novel, makes logical sense. These relatively straightforward steps can serve as a reassuring check that any proposed structure, if novel, makes logical sense This type of thought process does not provide hard evidence regarding a proposed structure, but it o en leads to important insights and realizations. If warranted, biomimetic synthetic studies or direct biosynthetic studies can be undertaken to probe the structure and origin of the natural product(s) further
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