ChemicalBook CAS DataBase List Ergosterol

Ergosterol synthesis

4synthesis methods

Product Name:Ergosterol
CAS Number:57-87-4
Molecular formula:C28H44O
Molecular Weight:396.65

Ergosterol is an important component of fungal cell membranes and is primarily obtained through industrial fermentation. Yeast strains, such as Saccharomyces cerevisiae, can naturally synthesize this compound via the mevalonate pathway. This biosynthetic pathway involves farnesyl pyrophosphatase-catalyzed conversion to squalene, followed by squalene cyclization to lanosterol, and then a series of subsequent demethylation, oxidation, and desaturation steps to finally produce ergosterol. While total chemical synthesis is useful for research, large-scale production relies on optimizing fermentation conditions and using synthetic biology techniques to modify yeast metabolic pathways to increase yield.

4a,13b-Etheno-1H,9H-benzo[c]cyclopenta[h][1,2,4]triazolo[1,2-a]cinnoline-1,3(2H)-dione, 6,8-bis(acetyloxy)-5,6,7,8,8a,8b,10,10a,11,12,13,13a-dodecahydro-11-(2-hydroxy-1-methylethyl)-8a,10a-dimethyl-2-phenyl-, [4aS-[4aα,6α,8β,8aα,8bβ,10aα,11α(R*),13aβ,13bα]]- (9CI)

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Yield:-

Steps:

Multi-step reaction with 9 steps
1: pyridine / 4 h / Ambient temperature
2: 1) NaI / 1) DMF, 30 min, 80 deg C, 2) 30 min, 80 deg C
3: 79 percent / KOH / methanol / 0.5 h / Heating
4: 90 percent / PPTS / CH₂Cl₂ / 24 h / Ambient temperature
5: 1) BuLi, HMPA / 1) THF, -78 deg C to -20 deg C, 20 min, 2) THF, -20 deg C, 1.5h
6: 53 percent / sodium amalgam (5percent), Na₂HPO₄ / methanol / 16 h / Ambient temperature
7: 83 percent / p-TsOH*H₂O, 95percent EtOH / 4 h / 80 °C
8: 86 percent / LiAlH₄ / tetrahydrofuran / Heating
9: 25 percent / diethyl ether; tetrahydrofuran / 0.05 h / Irradiation

References:

Tsuji;Yokoyama;Tachibana;Ikekawa [Bulletin of the Chemical Society of Japan,1990,vol. 63,# 8,p. 2233 - 2238]

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References

4a,13b-Etheno-1H,9H-benzo[c]cyclopenta[h][1,2,4]triazolo[1,2-a]cinnoline-1,3(2H)-dione, 6-(benzoyloxy)-5,6,7,8,8a,8b,10,10a,11,12,13,13a-dodecahydro-8a,10a-dimethyl-11-(1,4,5-trimethyl-2-hexenyl)-, [4aS-[4aα,6α,8aα,8bβ,10aα,11α(1S*,2E,4S*),13aβ,13bα]]- (9CI)

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References

4a,13b-Etheno-1H,9H-benzo[c]cyclopenta[h][1,2,4]triazolo[1,2-a]cinnoline-11-acetaldehyde, 6,8-bis(acetyloxy)-2,3,5,6,7,8,8a,8b,10,10a,11,12,13,13a-tetradecahydro-α,8a,10a-trimethyl-1,3-dioxo-2-phenyl-, [4aS-[4aα,6α,8β,8aα,8bβ,10aα,11α(R*),13aβ,13bα]]- (9CI)

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References

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Ergosterol synthesis

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