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A unique electron-accepting analog of vitamin K1 found in photosystem I in several species of oxygenic photosynthetic microorganisms was confirmed to be 5′-hydroxyphylloquinone (1) through stereo-uncontrolled synthesis. Furthermore, the stereochemistry of 1 obtained from Synechococcus sp. PCC 7942 was assigned to be 5′S using proline-catalyzed stereocontrolled reactions.

Stereochemical assignment of the unique electron acceptor 5′-hydroxyphylloquinone, a polar analog of vitamin K1 in photosystem I