Unknown

Dataset Information

0

Total Synthesis of 6-Deoxydihydrokalafungin, a Key Biosynthetic Precursor of Actinorhodin, and Its Epimer


ABSTRACT: In this article, we report the total synthesis of 6-deoxydihydrokalafungin (DDHK), a key biosynthetic intermediate of a dimeric benzoisochromanequinone antibiotic, actinorhodin (ACT), and its epimer, epi-DDHK. Tricyclic hemiacetal with 3-siloxyethyl group was subjected to Et3SiH reduction to establish the 1,3-cis stereochemistry in the benzoisochromane, and a subsequent oxidation/deprotection sequence then afforded epi-DDHK. A bicyclic acetal was subjected to AlH3 reduction to deliver the desired 1,3-trans isomer in an approximately 3:1 ratio, which was subjected to a similar sequence to that used for the 1,3-cis isomer that successfully afforded DDHK. A semisynthetic approach from (S)-DNPA, an isolable biosynthetic precursor of ACT, was also examined to afford DDHK and its epimer, which are identical to the synthetic products.

SUBMITTER: Kumamoto T 

PROVIDER: S-EPMC8587838 | biostudies-literature |

REPOSITORIES: biostudies-literature

Similar Datasets

| S-EPMC3869251 | biostudies-literature
| S-EPMC4651627 | biostudies-literature
| S-EPMC3256008 | biostudies-literature
| S-EPMC5386831 | biostudies-literature
| S-EPMC336920 | biostudies-other
| S-EPMC8328920 | biostudies-literature
| S-EPMC4464531 | biostudies-other
| S-EPMC11290413 | biostudies-literature
| S-EPMC3696528 | biostudies-literature
| S-EPMC3370682 | biostudies-literature