Total synthesis campaigns toward chlorophylls and related natural hydroporphyrins - diverse macrocycles, unrealized opportunities

Natural Product Reports
Yizhou LiuJonathan S Lindsey

Abstract

Covering: up to 2018 Chlorophylls, bacteriochlorophylls and related hydroporphyrins constitute invaluable natural products but have largely remained outside the scope of viable syntheses. The campaign toward chlorophyll a by Woodward and coworkers is a deservedly celebrated landmark in organic synthesis yet the route entailed 49 steps, relied on semisynthetic replenishment of advanced intermediates, and then pointed to (but did not implement) uncertain literature procedures for the final transformations. Indeed, the full synthesis at any scale of any (bacterio)chlorophylls - conversion of small-molecule starting materials to the product - has never been accomplished. Herein, the reported syntheses of (±)-bonellin dimethyl ester (0.93 mg) and tolyporphin A O,O-diacetate (0.38 mg), as well as the never-fully traversed route to chlorophyll a, have been evaluated in a quantitative manner. Bonellin and tolyporphin A are naturally occurring chlorin and bacteriochlorin macrocycles, respectively, that lack the characteristic fifth ring of (bacterio)chlorophylls. A practical assessment is provided by the cumulative reaction mass efficiency (cRME) of the entire synthetic process. The cRME for the route to chlorophyll a would be 4.3 × 10-...Continue Reading

References

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Citations

May 24, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ubaldina GalliGian Cesare Tron
Feb 25, 2021·Chemical Society Reviews·Mathias O SengeKarl J Hale
Mar 7, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chih-Hui YangJei-Fu Shaw
Oct 22, 2020·The Journal of Organic Chemistry·Nivedita ChaudhriChristian Brückner
Aug 21, 2019·The Journal of Organic Chemistry·Mario A NoboaTimothy D Lash
Aug 23, 2019·The Journal of Organic Chemistry·Pengzhi WangJonathan S Lindsey
Feb 8, 2020·Inorganic Chemistry·David SchnableChristian Brückner
May 5, 2020·The Journal of Organic Chemistry·Khiem Chau NguyenJonathan S Lindsey

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Methods Mentioned

BETA
acetylation
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