One-Pot Stereoselective Synthesis of Tricyclic Bislactones from 2-Pyrones and 2-Methoxyfuran

A one-pot synthesis of the title compounds via highly chemo-, regio-, and stereoselective Diels−Alder reactions of 2-pyrones with 2-methoxyfuran is described

First Total Syntheses of (±)-Penicillones A and B

The first total syntheses of (±)-penicillones A (1) and B (2) have been accomplished from 2-methoxy-4,6-dimethylphenol (7) in 9 and 8 synthetic steps, respectively. Intramolecular Diels−Alder reaction of masked o-benzoquinone 8 and aqueous acid-catalyzed intramolecular aldol reaction are the key steps

1,3-Methoxy Rearrangement of Masked <i>o</i>-Benzoquinones: A Novel Synthesis of <i>p</i>-Quinol Ethers

p-Quinol ethers are valuable synthons in synthetic organic chemistry. MOBs 1a−1i can be converted to p-quinol ethers 2a−2i in a highly efficient manner via 1,3-methoxy migration catalyzed by Lewis acids. The migration was found to be reversible and dependent on the electronic effect of substituent R3 of MOBs

First Total Syntheses of (±)-Penicillones A and B

The first total syntheses of (±)-penicillones A (1) and B (2) have been accomplished from 2-methoxy-4,6-dimethylphenol (7) in 9 and 8 synthetic steps, respectively. Intramolecular Diels−Alder reaction of masked o-benzoquinone 8 and aqueous acid-catalyzed intramolecular aldol reaction are the key steps

Total Syntheses of Sesterpenic Acids: Refuted (±)-Bilosespenes A and B

The total syntheses of racemic sesterpenic acids 1 and 2 have been accomplished from creosol (6) in 12 and 13 steps, respectively. Intramolecular Diels−Alder reaction of masked o-benzoquinone 7 generated from 6 and allyl alcohol, stereoselective addition of alkenylcerium(III) chloride 8 to ketone 5, and anionic oxy-Cope rearrangement of dienol 4 are the key steps

Total Syntheses of Sesterpenic Acids: Refuted (±)-Bilosespenes A and B

The total syntheses of racemic sesterpenic acids 1 and 2 have been accomplished from creosol (6) in 12 and 13 steps, respectively. Intramolecular Diels−Alder reaction of masked o-benzoquinone 7 generated from 6 and allyl alcohol, stereoselective addition of alkenylcerium(III) chloride 8 to ketone 5, and anionic oxy-Cope rearrangement of dienol 4 are the key steps

First Asymmetric Total Syntheses and Determination of Absolute Configurations of (+)-Eudesmadiene-12,6-olide and (+)-Frullanolide

The first asymmetric total syntheses of sesquiterpene lactones (+)-eudesmadiene-12,6-olide (<b>1</b>) and (+)-frullanolide (<b>2</b>) have been accomplished from 4-bromo-2-methoxyphenol (<b>5</b>) in 12 and 13 synthetic steps, respectively, and the absolute configurations of these two natural products were determined

Furans Act as Dienophiles in Facile Diels−Alder Reactions with Masked <i>o-</i>Benzoquinones

Furans Act as Dienophiles in Facile Diels−Alder Reactions with Masked o-Benzoquinone

Application of Carbohydrate-Templated Asymmetric Diels–Alder Reaction to the Syntheses of <i>ent</i>-Penicillones A and B

Total syntheses of ent-penicillones A (ent-1) and B (ent-2) from 3,5-dimethylcatechol (3) were accomplished in 10 and 9 synthetic steps, respectively. A carbohydrate-templated asymmetric intramolecular Diels–Alder reaction of a masked o-benzoquinone (MOB) 9 and an aqueous acid-catalyzed intramolecular aldol reaction are the key synthetic steps. In addition, the absolute configurations of the bicyclo[2.2.2]­oct-5-en-2-one core obtained from the per-O-benzylated α-d-glucopyranosyl as a carbohydrate template in the intramolecular Diels–Alder reaction of MOBs were revised

First Total Syntheses of (±)-Annuionone B and (±)-Tanarifuranonol

The intramolecular Diels−Alder reaction of o-quinol allyl ether was accomplished and subsequently applied to the first total syntheses of natural products annuionone B (1) and both the proposed and revised structure of tanarifuranonol, 4 and 17